GB699111A - Production of pyrrolinones - Google Patents

Production of pyrrolinones

Info

Publication number
GB699111A
GB699111A GB2260/51A GB226051A GB699111A GB 699111 A GB699111 A GB 699111A GB 2260/51 A GB2260/51 A GB 2260/51A GB 226051 A GB226051 A GB 226051A GB 699111 A GB699111 A GB 699111A
Authority
GB
United Kingdom
Prior art keywords
acetoacetamido
aceto
prepared
sodium
pyrrolin
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
GB2260/51A
Inventor
Richard Norman Lacey
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.)
British Industrial Solvents Ltd
Original Assignee
British Industrial Solvents Ltd
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 British Industrial Solvents Ltd filed Critical British Industrial Solvents Ltd
Priority to GB2260/51A priority Critical patent/GB699111A/en
Publication of GB699111A publication Critical patent/GB699111A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrrole Compounds (AREA)

Abstract

3 - Aceto - D 3 - pyrrolin - 4 - ol - 2 - one and derivatives of general formula <FORM:0699111/IV (b)/1> where R1, R2 and R3 may be hydrogen, lower alkyl, aryl, substituted aryl, aralkyl or alicyclic groups, are prepared by treatment of an acetoacetic acid amide of general formula <FORM:0699111/IV (b)/2> (where R4 is lower alkyl) with a substance capable of effecting a Claisen condensation whereby an alcohol group is eliminated. The reaction may be conducted in a solvent, such as benzene, toluene or a lower aliphatic alcohol, and particular condensing agents are sodium, potassium, their alkoxides, triphenyl methyl sodium, sodium hydride and sodamide. Typical acetoacetic acid amides include the ethyl esters of acetoacetamido acetic acid, a -acetoacetamido propionic acid and N-phenyl acetoacetamido acetic acid. These amides are prepared from a -amino acetic esters by treatment with diketene in inert organic solvents, benzene, chloroform (or ethanol under cooling conditions). Practical details are given. In examples: (1) 3 - aceto - D 3 - pyrrolin - 4 - ol - 2 - one is prepared from crude ethyl acetoacetamido, acetate in benzene by agitation with methanolic sodium methoxide, then aqueous extraction and acidification when the pyrrolinone is liberated; (2) 3 - aceto - D 3 - 5 - methylpyrrolin - 4 - ol - 2-one is prepared likewise from ethyl acetoacetamido propionate using ethanolic sodium ethoxide; and (3) 3-aceto-1-phenyl-D 3-pyrrolin-4-ol-2-one under the same conditions from the appropriate amide.
GB2260/51A 1951-01-30 1951-01-30 Production of pyrrolinones Expired GB699111A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2260/51A GB699111A (en) 1951-01-30 1951-01-30 Production of pyrrolinones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2260/51A GB699111A (en) 1951-01-30 1951-01-30 Production of pyrrolinones

Publications (1)

Publication Number Publication Date
GB699111A true GB699111A (en) 1953-10-28

Family

ID=9736414

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2260/51A Expired GB699111A (en) 1951-01-30 1951-01-30 Production of pyrrolinones

Country Status (1)

Country Link
GB (1) GB699111A (en)

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