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

HRID 637786

Reaction equation

HRID 637786 reaction equation
[NH3:1].[O:2]=[C:3]1[C:8]2[CH:9]=[CH:10]O[C:7]=2[CH2:6][CH2:5][CH2:4]1>C(O)C>[O:2]=[C:3]1[CH2:4][CH2:5][CH2:6][C:7]2[NH:1][CH:10]=[CH:9][C:8]1=2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 27335414,5,6,7-Tetrahydro-1-benzofuran-4-one

Product 1

HCID 2802291,5,6,7-Tetrahydro-4H-indol-4-oneYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 3 ml of ethanol and 7 ml of 29% aqueous ammonia was added 1.0 g of 4-oxo-4,5,6,7-tetrahydrobenzofuran, and then the mixture was subjected to reaction in a sealed tube at 150° C. for 12 hours. After completing the reaction, the reaction mixture was concentrated. The resulting residue was applied to a column of silica gel and eluted with a mixed solvent of acetone and ethyl acetate to give 950 mg (yield: 96%) of 4-oxo-4,5,6,7-tetrahydroindole being a light yellowish crystal.

Workup

  1. customthe mixture was subjected to reaction in a sealed tube at 150° C. for 12 hours
  2. customthe reaction
  3. concentrationthe reaction mixture was concentrated
  4. washeluted with a mixed solvent of acetone and ethyl acetate

Sources & evidence

ORD record
ord-6814b997cc814d20b1020941b9259c5c
Source dataset
uspto-grants-1985_12
Patent number
US04558143

Linked notes

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