Dimethylformamide → 5-Chloro-3-(2-chlorophenyl)-1,3-dihydro-3-(dimethylamino)-1-(4-nitrobenzyl)indol-2-one

HRID 234545Notes

Reaction equation

HRID 234545 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])[N:12]([CH3:14])[CH3:13].[H-].[Na+].CN(C=O)C.[N+:29]([C:32]1[CH:39]=[CH:38][C:35]([CH2:36]Br)=[CH:34][CH:33]=1)([O-:31])=[O:30]>C(Cl)Cl.CCCCCC.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:36][C:35]1[CH:38]=[CH:39][C:32]([N+:29]([O-:31])=[O:30])=[CH:33][CH:34]=1)[C:6](=[O:11])[C:5]2([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])[N:12]([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromideHCID 190765485-Chloro-3-(2-chlorophenyl)-1,3-dihydro-3-dimethylaminoindol-2-one

Product 1

HCID 190764365-Chloro-3-(2-chlorophenyl)-1,3-dihydro-3-(dimethylamino)-1-(4-nitrobenzyl)indol-2-oneYield 92.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

This compound is prepared according to the procedure described in EXAMPLE 89 from 1 g of 5-chloro-3-(2-chlorophenyl)-1,3-dihydro-3-(dimethylamino)indol-2-one, 0.132 g of sodium hydride as a 60% dispersion in oil, 5 ml of DMF and 0.741 g of 4-nitrobenzyl bromide. Chromatography on silica using a DCM/hexane mixture (80/20; v/v) and then DCM as the eluent gives 1.32 g of the expected product after crystallization from a DCM/iso ether mixture. M.p.=189°-193° C.

Workup

  1. customThis compound is prepared

Sources & evidence

ORD record
ord-f450955a9a144e729874b78b33011d56
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

Loading…