GB819654A - New quinone derivatives and a process for their preparation - Google Patents

New quinone derivatives and a process for their preparation

Info

Publication number
GB819654A
GB819654A GB475856A GB475856A GB819654A GB 819654 A GB819654 A GB 819654A GB 475856 A GB475856 A GB 475856A GB 475856 A GB475856 A GB 475856A GB 819654 A GB819654 A GB 819654A
Authority
GB
United Kingdom
Prior art keywords
give
benzoquinone
trichloro
blue
quinone
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
GB475856A
Inventor
Harold Bernard Henbest
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.)
National Research Development Corp UK
Original Assignee
National Research Development Corp UK
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 National Research Development Corp UK filed Critical National Research Development Corp UK
Priority to GB475856A priority Critical patent/GB819654A/en
Publication of GB819654A publication Critical patent/GB819654A/en
Expired legal-status Critical Current

Links

Abstract

The invention comprises aminovinyl quinones of the general formula #f[-CR=CH.NR1R2]n where #f is a quinone residue which may be unsubstituted or substituted in the quinone ring by one or more electronegative groups or atoms, R is hydrogen or an alkyl group containing up to 5 carbon atoms, R1 is an alkyl or hydroxyalkyl group, R2 is an alkyl, hydroxyalkyl, aralkyl or aryl group or R1 and R2 together with the nitrogen atom form a saturated heterocyclic ring and n is either 1 or 2, the groups R1 and R2 being unsubstituted or substituted by groups other than strongly electronegative groups. The preferred compounds are those where all the carbon atoms in the quinone ring are substituted by chloro and/or methoxy groups, R is hydrogen, R1 methyl, ethyl or hydroxyethyl, R2 methyl, ethyl, hydroxyethyl or phenyl or together with R1 and the nitrogen form a morpholine ring. The compounds may be prepared by treating a quinone having at least one position reactive to a nucleophillic reagent with an aldehyde of the formula R.CH2CHO and a secondary amine of the formula HN.R1R2 where R, R1 and R2 are as above. The reaction may be carried out in an inert non-acidic solvent, e.g. benzene, ether, dioxan or light petroleum, at room temperature or slightly above. In the examples, tetrachloro-p-benzoquinone and acetaldehyde are treated with (1) diethylamine to give the blue 2,3,5-trichloro - 6 - diethylaminovinyl - p - benzoquinone, (2) dimethylamine to give the blue 2,3,5 - trichloro - 6 - dimethylaminovinyl - p - benzoquinone, (3) morpholine to give the blue 2,3,5 - trichloro - 6 - morpholinovinyl - p - benzoquinone, (4) diethanolamine to give the blue 2,3,5 - trichloro - 6 - di - (hydroxyethyl) aminovinyl - p - benzoquinone, (5) methylaniline to give the blue 2,3,5-trichloro-6-methylanilinovinyl-p-benzoquinone, (7) as (1) but using double the amount of diethylamine to give 2,5-dichloro - 3,6 - bis - diethylaminovinyl - p - benzoquinone, (6) 3,5 - dichloro - 2,6 - dimethoxy - p - benzoquinone is treated with acetaldehyde and diethylamine to give 3,5-dichloro - 2 - methoxy - 6 - diethylaminovinyl-p - benzoquinone; 2,3 - dichloro - naphthaquinone is treated with acetaldehyde, and (8) dimethylamine to give the red 2-chloro-3-(21-dimethylaminovinyl) - 1,4 - naphthaquinone, and (9) diethylamine to give the red 2-chloro-3-(21-diethylaminovinyl)-1,4-naphthaquinone.ALSO:The invention comprises aminovinyl quinones of the general formula #f[-CR=CH.NR1R2]n where #f is a quinone residue which may be unsubstituted or substituted in the quinone ring by one or more electronegative groups or atoms, R is hydrogen or an alkyl group containing up to 5 carbon atoms, R1 is an alkyl or hydroxyalkyl group, R2 is an alkyl, hydroxyalkyl, aralkyl or aryl group or R1 and R2 together with the nitrogen atom form a saturated heterocyclic ring and n is either 1 or 2, the groups R1 and R2 being unsubstituted or substituted by groups other than strongly electronegative groups. The compounds are said to find application as dyes and the preferred compounds are those where all the carbon atoms in the quinone ring are substituted by chloro and/or methoxy groups, R is hydrogen, R1 methyl, ethyl or hydroxyethyl, R2 methyl, ethyl, hydroxyethyl or phenyl or together with R1 and the nitrogen form a morpholine ring. The compounds may be prepared by treating a quinone having at least one position reactive to a nucleophillic reagent with an aldehyde of the formula R.CH2CHO and a second amine of the formula HN.R1R2, where R, R1 and R2 are as above. The reaction may be carried out in an inert non-acidic solvent, e.g. benzene, ether, dioxan or light petroleum, at room temperature or slightly above. In the examples tetrachloro-p-benzoquinone and acetaldehyde are treated with (1) diethylamine to give the blue 2,3,5-trichloro - 6 - diethylaminovinyl - p - benzo - quinone, (2) dimethylamine to give the blue 2,3,5 - trichloro - 6 - dimethylaminovinyl - p - benzoquinone, (3) morpholine to give the blue 2,3,5 - trichloro - 6 - morpholinovinyl - p - benzoquinone, (4) diethanolamine to give the blue 2,3,5 - trichloro - 6 - di - (hydroxyethyl) aminovinyl-p-benzoquinone, (5) methylaniline to give the blue 2,3,5-trichloro-6-methylanilinovinyl-p-benzoquinone, (7) as (1) but using double the amount of diethylamine to give 2,5 - dichloro - 3,6 - bis - diethylamino - vinyl-p-benzoquinone, (6) 3,5 - dichloro - 2,6 - dimeth - oxy-p-benzoquinone is treated with acetaldehyde and diethylamine to give 3,5-dichloro-2-methoxy - 6 - diethylaminovinyl - p - benzo - quinone; 2,3 - dichloro - naphthaquinone is treated with acetaldehyde and (8) dimethylamine to give the red 2-chloro-3-(21-dimethylaminovinyl) - 1,4 - naphthaquinone and (9) diethylamine to give the red 2-chloro-3-(21-diethylaminovinyl)-1,4-naphthaquinone.
GB475856A 1956-02-15 1956-02-15 New quinone derivatives and a process for their preparation Expired GB819654A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB475856A GB819654A (en) 1956-02-15 1956-02-15 New quinone derivatives and a process for their preparation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB475856A GB819654A (en) 1956-02-15 1956-02-15 New quinone derivatives and a process for their preparation

Publications (1)

Publication Number Publication Date
GB819654A true GB819654A (en) 1959-09-09

Family

ID=9783216

Family Applications (1)

Application Number Title Priority Date Filing Date
GB475856A Expired GB819654A (en) 1956-02-15 1956-02-15 New quinone derivatives and a process for their preparation

Country Status (1)

Country Link
GB (1) GB819654A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0092136A1 (en) * 1982-04-13 1983-10-26 Takeda Chemical Industries, Ltd. Benzoquinone derivatives and production thereof
US4808339A (en) * 1982-04-13 1989-02-28 Takeda Chemical Industries, Ltd. Benzoquinone derivatives

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0092136A1 (en) * 1982-04-13 1983-10-26 Takeda Chemical Industries, Ltd. Benzoquinone derivatives and production thereof
US4751303A (en) * 1982-04-13 1988-06-14 Takeda Chemical Industries, Ltd. Benzoquinone derivatives and production thereof
US4808339A (en) * 1982-04-13 1989-02-28 Takeda Chemical Industries, Ltd. Benzoquinone derivatives
US4874752A (en) * 1982-04-13 1989-10-17 Takeda Chemical Industries, Ltd. Benzoquinone derivatives and production thereof
US4943645A (en) * 1982-04-13 1990-07-24 Takeda Chemical Industries, Ltd. Benzoquinone derivatives and production thereof

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