Nitromethane → 1-Benzhydryl-6-chloro-2-(2-nitro-vinyl)-1H-indole

HRID 2237096Notes

Reaction equation

HRID 2237096 reaction equation
[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([Cl:23])[CH:21]=2)[CH:16]=[C:15]1[CH:24]=O)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:26]([CH3:29])([O-:28])=[O:27]>CCOC(C)=O>[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([Cl:23])[CH:21]=2)[CH:16]=[C:15]1[CH:24]=[CH:29][N+:26]([O-:28])=[O:27])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6375NitromethaneHCID 161163341-benzhydryl-6-chloro-1H-indole-2-carbaldehyde

Product 1

HCID 670554211-Benzhydryl-6-chloro-2-(2-nitro-vinyl)-1H-indoleYield 48%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-benzhydryl-6-chloro-1H-indole-2-carbaldehyde (0.5M, 1 equiv.) and NH4OAc (1 equiv.) in nitromethane was heated at 95° C. for 70 min. The mixture was diluted with EtOAc, washed with water, and dried. Evaporation of the volatiles, followed by trituration with ether/hexane produced 1-Benzhydryl-6-chloro-2-(2-nitro-vinyl)-1H-indole in 48% yield.

Workup

  1. washwashed with water
  2. customdried
  3. customEvaporation of the volatiles

Sources & evidence

ORD record
ord-31b258fd4532475bbe1616ced8285edd
Source dataset
uspto-grants-2010_05
Patent number
US07713964B2

Reaction notes

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