1,3-Cyclohexanedione → 6-Methoxy-1,2,3,9-tetrahydro-4H-carbazol-4-one

HRID 4379

Reaction equation

HRID 4379 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=O)[CH2:2]1.Cl.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18]N)=[CH:14][CH:13]=1>C(O)C.O>[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:15](=[CH:16][CH:17]=1)[NH:18][C:3]1[CH2:4][CH2:5][CH2:6][C:1](=[O:8])[C:2]2=1

Participants

5

Reactant 2

HCID 104341,3-CyclohexanedioneHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 152128016-Methoxy-1,2,3,9-tetrahydro-4H-carbazol-4-oneYield 48.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

1,3-Cyclohexanedione (8 g) was added to a solution of 4-methoxyphenylhydrazine hydrochloride (10 g) in ethanol (350 ml) and water (70 ml). The resulting solution was stirred at room temperature for 3 h and then at reflux for 14 h. On cooling to ambient temperature, the reaction mixture was poured into water (3 l) to give a solid, which was dried in vacuo to give the title compound, (6.0 g) m.p. 279°-279.5°.

Workup

  1. temperatureat reflux for 14 h
  2. temperatureOn cooling to ambient temperature
  3. customto give a solid, which
  4. customwas dried in vacuo

Sources & evidence

ORD record
ord-313df49ceb1b4c6cb32f2cf23619645d
Source dataset
uspto-grants-1988_02
Patent number
US04725615

Linked notes

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