Nitromethane → 6-chloro-3-[(E)-2-nitrovinyl]-5-(trifluoromethyl)-1H-indole

HRID 1670742Notes

Reaction equation

HRID 1670742 reaction equation
C([O-])(=O)C.[NH4+].[Cl:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH:16]=O)=[CH:12][NH:13]2)=[CH:9][C:8]=1[C:18]([F:21])([F:20])[F:19].[N+:22]([CH3:25])([O-:24])=[O:23]>>[Cl:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11](/[CH:16]=[CH:25]/[N+:22]([O-:24])=[O:23])=[CH:12][NH:13]2)=[CH:9][C:8]=1[C:18]([F:21])([F:20])[F:19]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 860655846-Chloro-5-(trifluoromethyl)indole-3-carbaldehyde

Product 1

HCID 231499866-chloro-3-[(E)-2-nitrovinyl]-5-(trifluoromethyl)-1H-indoleYield 49%

Procedure

Nitromethane (20 ml) and ammonium acetate (1.6 g) were added to 6-chloro-5-(trifluoromethyl)indole-3-carbaldehyde (3.25 g) and the mixture was heated under reflux for 1 hr. The reaction mixture was allowed to cool, and the precipitated solid was collected by filtration, washed with methanol-water (1:1) and dried to give a brown solid. This solid was washed in a suspension state with diethyl ether, collected by filtration and dried to give 6-chloro-3-[(E)-2-nitrovinyl]-5-(trifluoromethyl)-1H-indole (1.86 g, yield 49%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. temperatureto cool
  4. filtrationthe precipitated solid was collected by filtration
  5. washwashed with methanol-water (1:1)
  6. customdried
  7. customto give a brown solid
  8. washThis solid was washed in a suspension state with diethyl ether
  9. filtrationcollected by filtration
  10. customdried

Sources & evidence

ORD record
ord-eabc0d43f584407fba21b2f7c8736e10
Source dataset
uspto-grants-2011_08
Patent number
US07994196B2

Reaction notes

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