Nitromethane → 3-(2-nitroethenyl)-1-phenylindole

HRID 1632918Notes

Reaction equation

HRID 1632918 reaction equation
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH:16]=O)=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+].[N+:23]([CH3:26])([O-:25])=[O:24]>CCOCC>[N+:23]([CH:26]=[CH:16][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 123779261-Phenyl-1H-indole-3-carbaldehyde

Product 1

HCID 6220043-(2-nitroethenyl)-1-phenylindole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

120 g 1-phenylindole-3-carboxaldehyde and 16.2 g ammonium acetate are heated under reflux in 406 ml nitromethane for 5 hours. The mixture is cooled, diluted with ether to give 3-(2-nitroethenyl)-1-phenylindole, m.p. 154°-155°.

Workup

  1. temperatureThe mixture is cooled

Sources & evidence

ORD record
ord-8e9b440b800d4652a96cbb38cdffdc6a
Source dataset
uspto-grants-1984_10
Patent number
US04478750

Reaction notes

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