Methanol → 1-(4-Aminobenzyl)-5-chloro-3-(2-chlorophenyl)-1,3-dihydro-3-(dimethylamino)indol-2-one

HRID 965593Notes

Reaction equation

HRID 965593 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)[C:6](=[O:21])[C:5]2([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31])[N:22]([CH3:24])[CH3:23].CO>[Ni].C1COCC1>[NH2:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:7]2[C:8]3[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)[C:5]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])([N:22]([CH3:23])[CH3:24])[C:6]2=[O:21])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 190764365-Chloro-3-(2-chlorophenyl)-1,3-dihydro-3-(dimethylamino)-1-(4-nitrobenzyl)indol-2-one

Product 1

HCID 190765851-(4-Aminobenzyl)-5-chloro-3-(2-chlorophenyl)-1,3-dihydro-3-(dimethylamino)indol-2-oneYield 90%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.88 g of the compound obtained in EXAMPLE 245, 0.9 g of Raney® nickel, 40 ml of MeOH and 40 ml of THF is hydrogenated at atmospheric pressure for 2 hours at RT. The catalyst is filtered off on Celite® and the filtrate is evaporated under vacuum. The residue is chromatographed on silica using DCM and then a DCM/AcOEt mixture (95/5; v/v) as the eluent to give 1.58 g of the expected product, which is used as such.

Workup

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

Sources & evidence

ORD record
ord-a016698ca52d48b7aeda9907dc6765b9
Source dataset
uspto-grants-1998_06
Patent number
US05773612

Reaction notes

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