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GB883803A - 1-phenyl-3, 3-dimethyl-spiro [(2h-1-benzopyran)-2, 2-indoline] and its derivatives - Google Patents

1-phenyl-3, 3-dimethyl-spiro [(2h-1-benzopyran)-2, 2-indoline] and its derivatives

Info

Publication number
GB883803A
GB883803A GB23082/60A GB2308260A GB883803A GB 883803 A GB883803 A GB 883803A GB 23082/60 A GB23082/60 A GB 23082/60A GB 2308260 A GB2308260 A GB 2308260A GB 883803 A GB883803 A GB 883803A
Authority
GB
United Kingdom
Prior art keywords
dimethyl
phenyl
indoline
methylene
condensing
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
Application number
GB23082/60A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
NCR Voyix Corp
National Cash Register Co
Original Assignee
NCR Corp
National Cash Register Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by NCR Corp, National Cash Register Co filed Critical NCR Corp
Publication of GB883803A publication Critical patent/GB883803A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/685—Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Color Printing (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

The invention comprises 1 - phenyl - 3,3 - dimethyl - spiro[(21H - 11 - benzopyran) - 2,21 indoline] having the structure <FORM:0883803/IV (b)/1> and its derivatives having the structure <FORM:0883803/IV (b)/2> in which R1, R2 and R3 represent stericall compatible substituents attached to one or more of the unoccupied positions of the benzene rings selected from CH3, CH2CH3, CH(CH3)2, C(CH3)3, C6H5, CF3, CN, COCH3, COOC2H5, COOH, NH2, NHCH3, N(CH3)2, NHCOCH3, NO2, OCH3, OC2H5, O(CH2)2CH3, O(C6H5), OH, OCOCH3, SCH3, SH, SCOCH3, SCN, SOCH3, SO2CH3, SO2NH2, F, Cl, Br, I, IO2, CH2CH= CH2, and COOCH3. These compounds may be prepared by condensing 1-phenyl-3,3-dimethyl-2-methyleneindoline or a suitably substituted derivative thereof with salicylaldehyde or a suitably substituted derivative thereof. Preferably the reactants are dissolved in ethanol and refluxed until the required compound appears in solid form. Examples are given of the p preparation of 1 - phenyl - 3.3 - dimethyl - spiro[(21H - 11- benzopyran)-2,21-indoline] without substituents and containing as substituents (a) an NO2 group in the 61 position or OCH3 in the 81 position; (b) an NO2 group in the 61 position and (c) NO2 groups in the 61 and 81 positions by condensing 1-phenyl-3,3-dimethyl-2-methyllene indoline with salicylaldehyde, 3-methoxy5 - nitrosalicylaldehyde, 5 - nitrosalicylaldehyde and 3.5-dinitrosalicylaldehyde respectively. A compound having chlorine radicals in the 5,7,211 and 411 positions is obtained by condensing salicylaldehyde with 1 - (2,4 - dichlorophenyl) - 3,3 - dimethyl - 2 - methylene - 5,7 - dichloroindolene. 1 - Phenyl - 3,3 - dimethyl - 2 - methylene indoline used as starting material may be prepared by (a) treating N-nitro diphenylamine with zinc dust and with hydrochloric acid to give N,N-diphenyl hydrazine hydrochloride, (b) condensing the diphenyl hydrazine hydrochloride with methyl isopropyl ketone to form the N,N-diphenyl hydrazone of methyl isopropyl ketone and (c) treating the hydrazone with zinc chloride to give the required 1-phenyl-3,3-dimethyl-2-methylene indoline. To get a substituted 1-phenyl-3.3-dimethyl-2-methylene indoline the correspondingly substituted diphenylamine is used as starting material. For example to obtain 1-(2,4-dichlorophenyl) - 3,3 - dimethyl - 2 - methylene - 5,7 - dichloroindoline 2,4,21,41 - tetrachloro diphenylamine is used as starting material.
GB23082/60A 1959-07-16 1960-07-01 1-phenyl-3, 3-dimethyl-spiro [(2h-1-benzopyran)-2, 2-indoline] and its derivatives Expired GB883803A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US82746259A 1959-07-16 1959-07-16
US191431A US3231584A (en) 1959-07-16 1962-05-01 1-phenyl-3, 3-dimethylspiro[(2'h-1'-benzopyran)-2', 2'-indoline] compound

Publications (1)

Publication Number Publication Date
GB883803A true GB883803A (en) 1961-12-06

Family

ID=26887043

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23082/60A Expired GB883803A (en) 1959-07-16 1960-07-01 1-phenyl-3, 3-dimethyl-spiro [(2h-1-benzopyran)-2, 2-indoline] and its derivatives

Country Status (6)

Country Link
US (1) US3231584A (en)
CH (1) CH395090A (en)
DE (1) DE1294382B (en)
FR (1) FR1262318A (en)
GB (1) GB883803A (en)
NL (2) NL253898A (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE623057A (en) * 1961-10-05
FR1394163A (en) * 1964-02-18 1965-04-02 Saint Gobain Photochromic compositions, in particular for the manufacture of variable transmission glazing
FR1451332A (en) * 1965-06-23 1966-01-07 Saint Gobain Novel di-spiropyran photochromic substances and process for preparing these substances
US3390192A (en) * 1965-10-20 1968-06-25 Geigy Chem Corp Dihydropyrenes and photochromic compositions based thereon
US3528926A (en) * 1966-10-27 1970-09-15 Ncr Co Mixed photochromic compound composition
US3507563A (en) * 1967-02-01 1970-04-21 Itek Corp Color-reversible anti-glare mirror
GB1245079A (en) * 1968-12-10 1971-09-02 Fuji Photo Film Co Ltd Spiro-indoline derivatives and their use in pressure-sensitive copying paper
FR2036168A5 (en) * 1969-03-06 1970-12-24 Saint Gobain
GB8610709D0 (en) * 1986-05-01 1986-06-04 Plinkington Bros Plc Photochromic lenses
GB8611837D0 (en) * 1986-05-15 1986-06-25 Plessey Co Plc Photochromic spiropyran compounds
GB8614680D0 (en) * 1986-06-17 1986-07-23 Plessey Co Plc Photoreactive lenses
IT1237528B (en) * 1989-12-12 1993-06-08 Enichem Sintesi SPIRO-OSSAZEPIN-OSSAZINE PHOTOCROMATIC AND THERMOCHROME COMPOUNDS AND PROCEDURE FOR THEIR PREPARATION
US5171636A (en) * 1989-12-12 1992-12-15 Enichem Synthesis S.P.A. Photochromatic and thermochromatic spiro-oxazepin-oxazine compounds and the process for their preparation

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE442515A (en) * 1940-07-30
BE566862A (en) * 1957-04-23
NL250081A (en) * 1959-04-03
US3085469A (en) * 1959-10-12 1963-04-16 Ncr Co Optical information-processing apparatus and method

Also Published As

Publication number Publication date
NL253898A (en)
US3231584A (en) 1966-01-25
CH395090A (en) 1965-07-15
NL127064C (en)
FR1262318A (en) 1961-05-26
DE1294382B (en) 1969-05-08

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