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

HRID 1156499Notes

Reaction equation

HRID 1156499 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.C(OC(OCC)CC1C(=O)CCCC1=O)C.[NH3:30]>CO>[O:5]=[C:6]1[CH2:7][CH2:8][CH2:9][C:10]2[NH:30][CH:4]=[CH:12][C:11]1=2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 110630394(2H)-Benzofuranone, 2-ethoxy-3,5,6,7-tetrahydro-HCID 20534715HCID 20534715, compound

Product 1

HCID 2802291,5,6,7-Tetrahydro-4H-indol-4-oneYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

The reactions of Examples 1 and 3 were respectively repeated and the reaction products were admixed in a molar (1)/(2) ratio of 87.6:12.4. Then, 1014 mg of this mixture of 2-ethoxy-4-oxo-2,3,4,5,6,7-hexahydrocoumarone and 2-(2',2'-diethoxyethyl)-1,3-cyclohexanedione, 1.7 ml of liquid ammonia and 5.5 ml of methanol were admixed in a glass tube which was sealed and heated at 100° C. for 1 hour and, then, at 150° C. for 16 hours. The above procedure provided 357.6 mg of 4-oxo-4,5,6,7-tetrahydroindole (yield 49%).

Workup

  1. customwhich was sealed

Sources & evidence

ORD record
ord-34db2fcc82ea45568d5b1563dcaf8f61
Source dataset
uspto-grants-1982_06
Patent number
US04336202

Reaction notes

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