GB787061A - Process for producing n-methyl--a-phenylsuccinimide - Google Patents

Process for producing n-methyl--a-phenylsuccinimide

Info

Publication number
GB787061A
GB787061A GB36461/55A GB3646155A GB787061A GB 787061 A GB787061 A GB 787061A GB 36461/55 A GB36461/55 A GB 36461/55A GB 3646155 A GB3646155 A GB 3646155A GB 787061 A GB787061 A GB 787061A
Authority
GB
United Kingdom
Prior art keywords
cyano
water
phenyl
prepared
ethyl
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
GB36461/55A
Inventor
Douglas Sydney Morris
Bruce Norman Feitelson
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.)
Parke Davis and Co LLC
Original Assignee
Parke Davis and Co LLC
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 Parke Davis and Co LLC filed Critical Parke Davis and Co LLC
Priority to GB36461/55A priority Critical patent/GB787061A/en
Publication of GB787061A publication Critical patent/GB787061A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
    • C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

N - methyl - a - phenylsuccinimide is prepared by reacting a b -substituted-a -phenyl-propionitrile of the formula <FORM:0787061/IV (b)/1> where in R represents a carboxylic acid ester group or a nitrile group, with at least two mols. of methylamine in the presence of water, e.g. at a temperature of 95 DEG to 200 DEG C., preferably in the neighbourhood of 105 DEG to 130 DEG C., and treating the resulting N,N-dimethyl-a -phenyl-succindiamide with a hydrohalic acid, e.g. hydrochloric acid. The methylamine reactant may be dissolved in water or a mixture of alcohol and water. In the examples N-methyl-a -phenyl-succinimide is prepared from b -cyano-a -phenyl-propionitrile and ethyl b -cyano-b -phenylpropionate. Starting materials. b -Cyano-a -phenylpropionitrile is prepared by reacting an alkyl ester of a -cyano-cinnamic acid with an alkali metal cyanide in the presence of water, e.g. ethyl a -cyano-cinnamate is reacted with sodium cyanide in the presence of water. Ethyl a -cyanocinnamate is prepared by reacting benzaldehyde and ethyl cyanoacetate in the presence of a few drops of piperidine. Specification 685,505 is referred to.
GB36461/55A 1955-12-20 1955-12-20 Process for producing n-methyl--a-phenylsuccinimide Expired GB787061A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB36461/55A GB787061A (en) 1955-12-20 1955-12-20 Process for producing n-methyl--a-phenylsuccinimide

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB36461/55A GB787061A (en) 1955-12-20 1955-12-20 Process for producing n-methyl--a-phenylsuccinimide

Publications (1)

Publication Number Publication Date
GB787061A true GB787061A (en) 1957-11-27

Family

ID=10388351

Family Applications (1)

Application Number Title Priority Date Filing Date
GB36461/55A Expired GB787061A (en) 1955-12-20 1955-12-20 Process for producing n-methyl--a-phenylsuccinimide

Country Status (1)

Country Link
GB (1) GB787061A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3453287A (en) * 1966-02-09 1969-07-01 Ernest E Campaigne Succinimido-(3,4-b)indan-8-ones and process

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3453287A (en) * 1966-02-09 1969-07-01 Ernest E Campaigne Succinimido-(3,4-b)indan-8-ones and process

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