Benzylamine → 1-benzyl-1,5,6,7-tetrahydro-4h-indol-4-one

HRID 1156501Notes

Reaction equation

HRID 1156501 reaction equation
C(O[CH:4]1[CH2:12][C:11]2[C:10](=[O:13])[CH2:9][CH2:8][CH2:7][C:6]=2O1)C.[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([N:21]1[C:6]2[CH2:7][CH2:8][CH2:9][C:10](=[O:13])[C:11]=2[CH:12]=[CH:4]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 110630394(2H)-Benzofuranone, 2-ethoxy-3,5,6,7-tetrahydro-

Product 1

HCID 2802711-benzyl-1,5,6,7-tetrahydro-4h-indol-4-oneYield 56%

Conditions

Temperature
110 °C

Procedure

A mixture of 182 mg of 2-ethoxy-4-oxo-2,3,4,5,6,7-hexahydrocoumarone and 1 ml of benzylamine was heated in a glass tube at 110° C. for 12 hours. The reaction mixture was purified by column chromatography on silica gel using a solvent mixture of ethyl acetate and n-hexane (1:1) to give 126 mg of N-benzyl-4-oxo-4,5,6,7-tetrahydroindole as white crystals (yield 56%). ##STR21##

Workup

  1. customThe reaction mixture was purified by column chromatography on silica gel using
  2. additiona solvent mixture of ethyl acetate and n-hexane (1:1)

Sources & evidence

ORD record
ord-b09176d0a4c6475d931680f31fa0b02c
Source dataset
uspto-grants-1982_06
Patent number
US04336202

Reaction notes

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