GB556266A - Improvements in and relating to polymethine dye intermediates and to the production of polymethine dyes - Google Patents
Improvements in and relating to polymethine dye intermediates and to the production of polymethine dyesInfo
- Publication number
- GB556266A GB556266A GB12486/41A GB1248641A GB556266A GB 556266 A GB556266 A GB 556266A GB 12486/41 A GB12486/41 A GB 12486/41A GB 1248641 A GB1248641 A GB 1248641A GB 556266 A GB556266 A GB 556266A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- butadienyl
- ethiodide
- iodide
- pyrrole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000975 dye Substances 0.000 title abstract 7
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 title 1
- -1 alkyl radical Chemical class 0.000 abstract 16
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 14
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 12
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 6
- 239000000543 intermediate Substances 0.000 abstract 5
- 150000003839 salts Chemical group 0.000 abstract 5
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- DXYYSGDWQCSKKO-UHFFFAOYSA-N methylbenzothiazole Natural products C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 abstract 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 3
- 229960000583 acetic acid Drugs 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 238000010992 reflux Methods 0.000 abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 239000012362 glacial acetic acid Substances 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 239000012429 reaction media Substances 0.000 abstract 2
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical compound C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 abstract 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 abstract 1
- PPXRSYKZGWZUQY-UHFFFAOYSA-N 1-ethyl-3-phenyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CC)CC(=O)N1C1=CC=CC=C1 PPXRSYKZGWZUQY-UHFFFAOYSA-N 0.000 abstract 1
- MCIPQLOKVXSHTD-UHFFFAOYSA-N 3,3-diethoxyprop-1-ene Chemical compound CCOC(C=C)OCC MCIPQLOKVXSHTD-UHFFFAOYSA-N 0.000 abstract 1
- UPCYEFFISUGBRW-UHFFFAOYSA-N 3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound CCN1C(=O)CSC1=S UPCYEFFISUGBRW-UHFFFAOYSA-N 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- FUFZNHHSSMCXCZ-UHFFFAOYSA-N 5-piperidin-4-yl-3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole Chemical compound FC(F)(F)C1=CC=CC(C=2N=C(ON=2)C2CCNCC2)=C1 FUFZNHHSSMCXCZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 241000009298 Trigla lyra Species 0.000 abstract 1
- 150000001241 acetals Chemical class 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- XTEGARKTQYYJKE-UHFFFAOYSA-M chlorate Inorganic materials [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 238000012216 screening Methods 0.000 abstract 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 abstract 1
- 150000003549 thiazolines Chemical class 0.000 abstract 1
- 125000005270 trialkylamine group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/10—The polymethine chain containing an even number of >CH- groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
556,266. Polymethine dyes and intermediates. KODAK, Ltd. Sept. 26, 1941, No. 12486. Convention date, Oct. 18, 1940. Samples furnished. [Class 2 (iii)] [Also in Group XX] A compound of the general formula of Fig. 1 where R represents an alkyl or aryl radical, R<SP>1</SP> represents an alkyl radical, X represents an acid radical, and Z the non-metallic atoms necessary to complete a 5- or 6- membered heterocyclic nucleus is prepared by condensing a #-alkoxyacrolein acetal with a cyclammonium quaternary salt containing a methyl group in the α-position to the nitrogen atom and employing as the reaction medium substantially anhydrous acetic acid not containing more than 1 per cent. of water. From 1 ¢ to 3 molecular proportions of acrolein acetal may be used for each molecular proportion of cyclammonium quaternary salt. The cyclammonium quaternary salt may be a quinoline, benzoxazole, naphthoxazole, benzthiazole, naphthathiazole, benzselenazole, or thiazoline derivative. The reaction medium may be glacial acetic acid and the quaternary salt an iodide. 2-(4-Ethoxy- #<SP>1</SP>:<SP>3</SP>-butadienyl)-benzthiazoleethiodide is prepared by reacting 2-methylbenzthiazole ethiodide and #-ethoxyacrolein diethyl acetal in glacial acetic acid. 2-(4-Ethoxy-#<SP>1</SP>:<SP>3</SP>-butadienyl)-benzoxazole ethiodide, 2-(4-etlaoxy-#<SP>1</SP>:<SP>3</SP>- butadienyl)-#-naphthathiazole ethiodide, 2-(4- ethoxy-#<SP>1</SP>:<SP>3</SP>-butadienyl)-α-naphthoxazole ethiodide, 2-(4-ethoxy-# <SP>1</SP>:<SP>3</SP>-butadienyl)-#-naphthoxazole ethiodide, 2-(4-ethoxy-#<SP>1</SP>:<SP>3</SP>-butadienyl)-quino line ethiodide, 2-(4-ethoxy-#<SP>1</SP>:<SP>3</SP>-butadienyl)-benzselenazole ethiodide, 2-(4-ethoxy- #<SP>1</SP>: <SP>3</SP>-butadienyl). thiazoline ethiodide, 2-(4-ethoxy-#<SP>1</SP>:<SP>3</SP>-butadienyl). benzthiazolepheniodide, and 2-(4-ethoxy-#<SP>1</SP>:<SP>3</SP>- butadienyl) 3:4 - - trimethylene benzthiazolium iodide are similarly prepared. Polymethine dyes are prepared by condensing a compound of the general formula shown in Fig. 1 with a cyclammonium alkyl quarternary salt containing a methyl group in the α or y position to the nitrogen atom. Pyridine or trialkylamines dissolved in acetic anhydride may be used as condensing agents. 3 : 3<SP>1</SP>- Diethylthiadicarbocyanine iodide is prepared by refluxing together 2 - (4 - ethoxy - # <SP>1</SP> : <SP>3</SP> - butadienyl) - benzthiazole ethiodide and 2 - methylbenzthiazole ethiodide in pyridine. 1<SP>1</SP>: 3- Diethyloxa - 2<SP>1</SP> - dicarbocyanine iodide is similarly prepared using as condensing agent acetic anhydride containing triethylamine. 1<SP>1</SP> : 3 - - Diethylthia - 2<SP>1</SP> dicarbocyanine iodide, 1<SP>1</SP> : 3 - diethylthia - 4<SP>1</SP> - dicarbocyanine iodide 3 : 3<SP>1</SP> - diethyl - 4 : 5 benzthiadicarbocyanine iodide, 3 : 3 - diethyl - 4 5 : 4<SP>1</SP>: 5<SP>1</SP> - dibenzthiadicarbocyanine iodide, 1 : : 1<SP>1</SP> - diethyl 2 : : 2<SP>1</SP>- dicarbocyanine iodide, 3 : 3<SP>1</SP> - diethyloxadi - carbocyanine iodide, 3 : 3<SP>1</SP> - . diethyloxathiadicarbonyanine isodide, 1<SP>1</SP> : 3 - diethyloxa - 4<SP>1</SP> - dicarbocyanine iodide, 3 3<SP>1</SP> - diethylselena - dicarbocyanine iodide, 3 : 3<SP>1</SP> - diethylselenathiadicarbocyanine iodide, 3 : 3<SP>1</SP>- diethyloxaselena dicarbocyanine iodide, and 3 - ethyl - 3<SP>1</SP> - methylthiathiazolino dicarbocyanine iodide are similarly prepared. Polymethine dyes may also be prepared by condensing the compounds of the general formula of Fig. 1 with a heterocyclic compound having a methylene group adjacent to a carbonyl group. 3 - - Ethyl - 5 - [(3 - - ethyl - 2 - benzthiazolyidene) - butenylidene] - rhodanine is prepared by condensing 2 - (4 - ethoxy - #<SP> 1</SP> : 3- butadienyl) - benzthiazole ethiodide with 3 - ethylrhodanine in the presence of triethylamine and acetic anhydride. The intermediate may also be condensed with 1 - phenyl - 3 - methyl - 5 -.pyrazolone or with 1 - ethyl - 3 - phenyl - 2 - thiohydantoin. Polymethine dyes may also be prepared by condensing the intermediates with primary or secondary aliphatic or aromatic amines. 2 - (4- Piper´dino - #<SP>1</SP> : <SP>3</SP> - butadienyl)- benzthiazole ethiodide is prepared by refluxing together 2 - (4 - ethoxy - #<SP>1</SP> : 3 - butadienyl)- benzthiazole ethiodide and piperidine in ethyl alcohol. The intermediate may also be condensed with aniline. Polymethine dyes may also be obtained by condensing the intermediates with N - alkyl or N - aryl pyrroles. Such dyes may be used as light-screening substances in the preparation of photographic elements, and are bleachable in alkaline developers. (3 - - Ethyl - 2 - benzthiazole) (1 - - heptyl - 2 : 5 - dimethyl - 3 - pyrrole) - tetramethinecyanine iodide is prepared by refluxing together 2 - (4 - ethoxy - #<SP>1</SP> : 3 - butadienyl) - benzthiazole ethiodide and 1 - heptyl - 2 : 5 - dimethylpyrrole in acetic anhydride. (3 - - Ethyl - 2 - benzoxazole) (1 - - heptyl - 2 : 5 - dimethyl - 3 pyrrole-, (3 - - ethyl - 2 - benzoxaozle) (1 - lauryl - 2 : : 5 - dimethyl 3 - - pyrrole) 3 - - ethyl - 2 - benzoxazole)- (1 - ethyl - 2 : : 5 - dimethyl - 3 - pyrrole)-, (1 - cetyl - 2 : 5 - dimethyl 3 - - pyrrole) 3 - - ethyl - 2 - benzoxazole)-, (1 ethyl - 2: 5 - dimethyl - 3 - pyrrole) - (3 - ethyl - 2 - α - naphthoxazole),- (3 - - ethyl - 2 - α - - naphthoxazole) - (1 lauryl - 2 : 5 - - dimethyl 3 - pyrrole)-, (1 - ethyl - 2 : 5 - dimethyl - 3 pyrrole) (1 - - ethyl - 2 - # - naphthoxazole)-, 1 - - ethyl - 2 5 - dimethyl - 3 pyrrole)- (1 - - ethyl 2 - quinoline)-, (3 - - ethyl - 2 - benzthia; zole)- (1 - ethyl - 2 : 5 - dimethyl - 3 pyrrole)-,. (3 - - ethyl - 2 - benzthiazole)- (2 : 5 dimethyl 1- phenyl 3 - - pyrrole)-, (1 - - ethyl - 2 : 5 - dimethyl- 3 - pyrrole) - (3 - - methyl - 2 thiazoline)-, and (3 - - ethyl - 2 - - benzselenazole) (1 - - ethyl - 2 : 5- dimethyl - 3 - pyrrole) tetramethine cyanines are similarly prepared. Samples have been furnished under Sect. 2 (5) of (a) 2<SP>1</SP> - (4 - methoxy - #<SP>1</SP> :<SP>3</SP> -butadienyl)- benzoxazole ethiodide (b) 2<SP>1</SP> - (4-piperidine - # <SP>1</SP>: <SP>3</SP> - butadienyl) - benzthiazole ethiodide: (c) 2<SP>1</SP> - (4 - anilino - #<SP>1</SP> : 3 - butadienyl) - benz - thiazole ethiodide : and (d) 2<SP>1</SP> - (4 - dibutylamino - # <SP>1</SP> : <SP>3</SP> - butadienyl) - benzoxazole ethoper - chlorate. Specification 551,331 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US556266XA | 1940-10-18 | 1940-10-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB556266A true GB556266A (en) | 1943-09-28 |
Family
ID=21999109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12486/41A Expired GB556266A (en) | 1940-10-18 | 1941-09-26 | Improvements in and relating to polymethine dye intermediates and to the production of polymethine dyes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB556266A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101726579A (en) * | 2008-10-17 | 2010-06-09 | 深圳迈瑞生物医疗电子股份有限公司 | Blood test reagent and method |
| CN101602762B (en) * | 2008-06-10 | 2013-10-16 | 深圳迈瑞生物医疗电子股份有限公司 | Asymmetric cyanine compound, preparation method and application thereof |
-
1941
- 1941-09-26 GB GB12486/41A patent/GB556266A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101602762B (en) * | 2008-06-10 | 2013-10-16 | 深圳迈瑞生物医疗电子股份有限公司 | Asymmetric cyanine compound, preparation method and application thereof |
| CN101726579A (en) * | 2008-10-17 | 2010-06-09 | 深圳迈瑞生物医疗电子股份有限公司 | Blood test reagent and method |
| CN101726579B (en) * | 2008-10-17 | 2014-06-18 | 深圳迈瑞生物医疗电子股份有限公司 | Blood test reagent and method |
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