Phenylacetone → 1,2-Dihydro-4-methyl-5-phenylpyrrolo[3,2,1-hi]indole

HRID 267235Notes

Reaction equation

HRID 267235 reaction equation
N[N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[C:11]1([CH2:17][C:18](=O)[CH3:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH3:19][C:18]1[N:2]2[C:10]3[C:5]([CH2:4][CH2:3]2)=[CH:6][CH:7]=[CH:8][C:9]=3[C:17]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7678PhenylacetoneHCID 517045Sodium AcetateHCID 6432211-Aminoindole

Product 1

HCID 112417811,2-Dihydro-4-methyl-5-phenylpyrrolo[3,2,1-hi]indole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 50 g. (0.372 mole) of 1-aminoindole, 50 g. (0.372 mole) of phenylacetone, 600 ml. of acetic acid and 50 g. of sodium acetate was heated for one hour on a steam bath. The precipitate which separated from the cooled mixture was collected and washed with isopropyl ether. The product melted at 145°C. The literature m.p. is 145°C., Chemical Abstracts 54, 19641 (1960).

Workup

  1. additionA mixture of 50 g
  2. customThe precipitate which separated from the cooled mixture
  3. customwas collected
  4. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-a81648fc66d14b4e932ce508b0c2a59e
Source dataset
uspto-grants-1976_03
Patent number
US03941806

Reaction notes

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