3-Amino-5-chloro-3-(2-chlorophenyl)-1,3-dihydro-1-(2-methoxy-4-nitrobenzenesulfonyl)indol-2-one → 3-Amino-1-(4-amino-2-methoxybenzenesulfonyl)-5-chloro-3-(2-chlorophenyl)-1,3-dihydroindol-2-one

HRID 965553Notes

Reaction equation

HRID 965553 reaction equation
[NH2:1][C:2]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[N:4]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][C:16]=2[O:24][CH3:25])(=[O:14])=[O:13])[C:3]1=[O:26].[H][H]>CO.C1COCC1.[Ni]>[NH2:1][C:2]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[N:4]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=2[O:24][CH3:25])(=[O:14])=[O:13])[C:3]1=[O:26]

Participants

6

Reactant 2

HCID 190765153-Amino-5-chloro-3-(2-chlorophenyl)-1,3-dihydro-1-(2-methoxy-4-nitrobenzenesulfonyl)indol-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 152844643-Amino-1-(4-amino-2-methoxybenzenesulfonyl)-5-chloro-3-(2-chlorophenyl)-1,3-dihydroindol-2-one

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.17 g of the compound obtained in EXAMPLE 16 in 30 ml of MeOH and 30 ml of THF are reduced with hydrogen under a pressure of 40 bar for 4 hours at RT, in the presence of 1 g of Raney nickel. The mixture is filtered on Celite and the filtrate is evaporated under vacuum. The residue is chromatographed on silica using DCM and then a DCM/AcOEt mixture (90/10; v/v) as the eluent to give the expected product after crystallization from a DCM/iso ether mixture. m=1.3 g. M.p.=198° C.

Workup

  1. filtrationThe mixture is filtered on Celite
  2. customthe filtrate is evaporated under vacuum
  3. customThe residue is chromatographed on silica

Sources & evidence

ORD record
ord-094c9953fe7a43258a9b378cf55b1285
Source dataset
uspto-grants-1998_06
Patent number
US05773612

Reaction notes

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