公开(公告)号：AU694840B2

公开(公告)日：1998-07-30

申请号：AU4767396

申请日：1996-01-25

Applicant: CATALYTICA INC

Inventor： GRUBER JOHN M ,  GRATE JOHN H ,  BULLS RAY A

IPC: C07C201/12 ,  C07C205/56 ,  C07D209/34 ,  C07C69/612

Abstract: The present invention provides a processes, having practical utility, for preparing 2-oxindoles, N-hydroxy-2-oxindoles, or mixtures thereof comprising: catalytically hydrogenating a 2-nitroarylmalonate diester to produce a 2-(N-hydroxyamino)arylmalonate diester, a 2-aminoarylmalonate diester, or mixtures thereof as a first reaction intermediate; cyclizing, by intramolecular aminolysis of one ester group, the first reaction intermediate to produce a N-hydroxy-2-oxindole-3-carboxylate ester, 2-oxindole-3-carboxylate ester, or mixtures thereof as a second reaction intermediate; and hydrolyzing and decarboxylating the remaining ester group of the second reaction intermediate to produce the N-hydroxy-2-oxindole, the 2-oxindole, or mixtures thereof, wherein the cyclization reaction and the hydrolysis and decarboxylation reaction are conducted in situ with the catalytic hydrogenation reaction without isolation of said reaction intermediates.

公开(公告)号：CA2210695A1

公开(公告)日：1996-08-08

申请号：CA2210695

申请日：1996-01-25

Applicant: CATALYTICA INC

Inventor： BULLS RAY A ,  GRUBER JOHN M

IPC: C07C201/12 ,  C07C205/56 ,  C07D209/34 ,  C07D491/04 ,  C07D495/04 ,  C07D209/60 ,  C07D209/70

Abstract: The present invention provides a processes, having practical utility, for preparing 2-oxindoles, N-hydroxy-2-oxindoles, or mixtures thereof comprising: catalytically hydrogenating a 2-nitroarylmalonate diester to produce a 2-(N-hydroxyamino)arylmalonate diester, a 2-aminoarylmalonate diester, or mixtures thereof as a first reaction intermediate; cyclizing, by intramolecular aminolysis of one ester group, the first reaction intermediate to produce a N-hydroxy-2-oxindole-3-carboxylate ester, 2-oxindole-3-carboxylate ester, or mixtures thereof as a second reaction intermediate; and hydrolyzing and decarboxylating the remaining ester group of the second reaction intermediate to produce the N-hydroxy-2-oxindole, the 2-oxindole, or mixtures thereof, wherein the cyclization reaction and the hydrolysis and decarboxylation reaction are conducted in situ with the catalytic hydrogenation reaction without isolation of said reaction intermediates.

公开(公告)号：EP0741702A4

公开(公告)日：1997-12-03

申请号：EP95908677

申请日：1995-01-27

Applicant: CATALYTICA INC

Inventor： GRUBER JOHN M

IPC: C07C273/18 ,  C07C275/54 ,  C07D209/34 ,  C07D223/10 ,  C07D209/32 ,  C07D209/56 ,  C07D291/02

CPC classification number: C07D223/10 ,  C07C273/1818 ,  C07D209/34 ,  C07C275/54

Abstract: The present invention provides a process for preparing 2-oxindole-1-carboxamides, comprising reacting N-acyl 2-oxindole-1-carboxamides with alcohols in the presence of aprotic weak Lewis acid catalysts. In certain processes of the present invention a 2-oxindole-1-carboxamide is prepared from a 2-oxindole by reacting the 2-oxindole with an acyl isocyanate to produce the N-acyl 2-oxindole-1-carboxamide as an intermediate, which is then reacted with alcohol in the presence of aprotic weak Lewis acid catalysts. The N-acyl 2-oxindole-1-carboxamide intermediate may be converted to the 2-oxindole-1-carboxamide without isolation.