GB1382259A - Process for producing quinacridones and intermediates thereof and said intermediates - Google Patents
Process for producing quinacridones and intermediates thereof and said intermediatesInfo
- Publication number
- GB1382259A GB1382259A GB6074271A GB6074271A GB1382259A GB 1382259 A GB1382259 A GB 1382259A GB 6074271 A GB6074271 A GB 6074271A GB 6074271 A GB6074271 A GB 6074271A GB 1382259 A GB1382259 A GB 1382259A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- alkyl
- intermediates
- nitrobenzene
- dec
- 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
- 239000000543 intermediate Substances 0.000 title 2
- 239000002253 acid Substances 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- 239000012670 alkaline solution Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 abstract 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 1
- RTZZCYNQPHTPPL-UHFFFAOYSA-N 3-nitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1 RTZZCYNQPHTPPL-UHFFFAOYSA-N 0.000 abstract 1
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 abstract 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 abstract 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 150000004682 monohydrates Chemical class 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 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
- C09B48/00—Quinacridones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
1382259 Acridanones TEKKOSHA KK 30 Dec 1971 [30 Dec 1970 (2)] 60742/71 Heading C2C [Also in Division C4] Compounds of formula where R 1 and R 3 are individually H, halogen, C 1-3 alkyl or C 1-3 alkoxy, and R 2 is H or C 1-3 alkyl, may be prepared by oxidizing the corresponding 1,4-dihydro compound in which R 2 is alkyl. If the oxidation is effected in alkaline solution and the product is neutralized with acid, the monohydrate of the free acid is formed, which may be dehydrated at 130-200‹ C. The oxidizing agent may be nitrobenzene, iodine, MnO 2 , FeCl 3 , benzoquinone, tetrachloro-pbenzoquinone, air, oxygen, Na nitrobenzene-msulphonate, m-nitrogenzoie acid, Na anthraquinone-sulphonate, or m-nitrophenol. The oxidation may be effected at 50-180‹ C. in a solvent, e.g. methanol., ethanol, propanol, butanol, N-methyl pyrrolidone, DMF, ethylene glycol, or ethylene glycol monoethyl ether. The alkaline solution may be aqueous NaOH and the neutralizing acid H 2 SO 4 . The starting materials are described in Specification 1,368,970.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12244570 | 1970-12-30 | ||
| JP12243970 | 1970-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1382259A true GB1382259A (en) | 1975-01-29 |
Family
ID=26459559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6074271A Expired GB1382259A (en) | 1970-12-30 | 1971-12-30 | Process for producing quinacridones and intermediates thereof and said intermediates |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE2165647A1 (en) |
| FR (1) | FR2120154B1 (en) |
| GB (1) | GB1382259A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4544746A (en) * | 1982-05-17 | 1985-10-01 | Ciba-Geigy Corporation | Process for preparing 2-anilinoacridone |
| US4937345A (en) * | 1987-10-10 | 1990-06-26 | Hoechst Aktiengesellschaft | Process for the preparation of 2-(arylamino)-3-carboxy-9(10H)-acridones |
| WO2003059269A3 (en) * | 2001-12-21 | 2003-12-31 | Bristol Myers Squibb Co | Acridone inhibitors of impdh enzyme |
| JP2024529394A (en) * | 2021-07-23 | 2024-08-06 | コンチネンタル・ライフェン・ドイチュラント・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | Compounds, rubber blends containing said compounds, vehicle tires containing said rubber blends as at least one component, processes for the manufacture of said compounds, and the use of said compounds as ageing stabilizers and/or antiozonants and/or dyes |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3515875A1 (en) * | 1985-05-03 | 1986-11-06 | Hoechst Ag, 6230 Frankfurt | METHOD FOR PRODUCING LINEAR CHINACRIDONES |
-
1971
- 1971-12-30 DE DE19712165647 patent/DE2165647A1/en active Pending
- 1971-12-30 GB GB6074271A patent/GB1382259A/en not_active Expired
- 1971-12-30 FR FR7147617A patent/FR2120154B1/fr not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4544746A (en) * | 1982-05-17 | 1985-10-01 | Ciba-Geigy Corporation | Process for preparing 2-anilinoacridone |
| US4937345A (en) * | 1987-10-10 | 1990-06-26 | Hoechst Aktiengesellschaft | Process for the preparation of 2-(arylamino)-3-carboxy-9(10H)-acridones |
| WO2003059269A3 (en) * | 2001-12-21 | 2003-12-31 | Bristol Myers Squibb Co | Acridone inhibitors of impdh enzyme |
| US6916809B2 (en) | 2001-12-21 | 2005-07-12 | Bristol-Myers Squibb Company | Heterocyclic acridone inhibitors of IMPDH enzyme |
| US7312209B2 (en) | 2001-12-21 | 2007-12-25 | Bristol-Myers Squibb Company | Acridone inhibitors of IMPDH enzyme |
| JP2024529394A (en) * | 2021-07-23 | 2024-08-06 | コンチネンタル・ライフェン・ドイチュラント・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | Compounds, rubber blends containing said compounds, vehicle tires containing said rubber blends as at least one component, processes for the manufacture of said compounds, and the use of said compounds as ageing stabilizers and/or antiozonants and/or dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2120154A1 (en) | 1972-08-11 |
| FR2120154B1 (en) | 1975-08-29 |
| DE2165647A1 (en) | 1972-07-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |