公开(公告)号：WO1996023770A1

公开(公告)日：1996-08-08

申请号：PCT/US1996000991

申请日：1996-01-25

Applicant: CATALYTICA, INC.

Inventor： CATALYTICA, INC. ,  GRUBER, John, M. ,  BULLS, Ray, A.

IPC: C07D209/34

CPC classification number: C07D209/34 ,  C07C201/12 ,  C07C253/30 ,  C07C205/56 ,  C07C255/41

Abstract: The present invention provides 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.

Abstract translation: 本发明提供了用于制备2-羟基吲哚，N-羟基-2-羟基吲哚或其混合物的实际应用的方法，其包括：催化氢化2-硝基芳基丙二酸二酯以产生2-（N-羟基氨基）芳基丙二酸二酯，2- 氨基芳基丙二酸二酯或其混合物作为第一反应中间体：通过一个酯基团的分子内氨基化来环化第一反应中间体以产生N-羟基-2-羟基吲哚-3-羧酸酯，2-羟基吲哚-3-羧酸酯 ，或其混合物作为第二反应中间体; 并将第二反应中间体的剩余酯基水解和脱羧以产生N-羟基-2-羟基吲哚，2-羟基吲哚或其混合物，其中环化反应和水解和脱羧反应与催化剂原位进行 不分离所述反应中间体的氢化反应。

公开(公告)号：EP0809631A1

公开(公告)日：1997-12-03

申请号：EP96903664.0

申请日：1996-01-25

Applicant: CATALYTICA, INC.

Inventor： GRUBBER, John, M. ,  BULLS, Ray, A.

IPC: C07C201 ,  C07C205 ,  C07D209

CPC classification number: C07D209/34 ,  C07C201/12 ,  C07C253/30 ,  C07C205/56 ,  C07C255/41

Abstract: The present invention provides 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.