Ammonia → 1,5,6,7-Tetrahydro-4H-indol-4-one

HRID 1156500Notes

Reaction equation

HRID 1156500 reaction equation
C(O[CH:4]1[CH2:12][C:11]2[C:10](=O)[CH2:9][CH2:8][CH2:7][C:6]=2[O:5]1)C.[NH3:14]>>[O:5]=[C:6]1[CH2:7][CH2:8][CH2:9][C:10]2[NH:14][CH:4]=[CH:12][C:11]1=2

Participants

3

Reactant 2

HCID 222AmmoniaHCID 110630394(2H)-Benzofuranone, 2-ethoxy-3,5,6,7-tetrahydro-

Product 1

HCID 2802291,5,6,7-Tetrahydro-4H-indol-4-oneYield 54%

Conditions

Temperature
100 °C

Procedure

96.5 mg of 2-ethoxy-4-oxo-2,3,4,5,6,7-hexahydrocoumarone and 1.5 ml of 28% aqueous ammonia were admixed in a glass tube which was sealed and heated at 100° C. for 14 hours. The reaction mixture was treated in the same manner as Example 11 to give 38.4 mg of 4-oxo-4,5,6,7-tetrahydroindole (yield 54%).

Workup

  1. customwhich was sealed
  2. additionThe reaction mixture was treated in the same manner as Example 11

Sources & evidence

ORD record
ord-116ca53683b0484f8e251164ad5c75b5
Source dataset
uspto-grants-1982_06
Patent number
US04336202

Reaction notes

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