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1,3-Cyclohexanedione → 1,2,3,9-Tetrahydro-6-(phenylmethoxy)-4H-carbazol-4-one

HRID 4382
Notes
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Reaction equation

HRID 4382 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=O)[CH2:2]1.Cl.[C:10]1([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24]N)=[CH:20][CH:19]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C.O>[C:10]1([CH2:16][O:17][C:18]2[CH:19]=[C:20]3[C:21](=[CH:22][CH:23]=2)[NH:24][C:3]2[CH2:4][CH2:5][CH2:6][C:1](=[O:8])[C:2]3=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 104341,3-CyclohexanedioneHCID 3016725(4-(Benzyloxy)phenyl)hydrazine monohydrochloride

Product 1

HCID 201524471,2,3,9-Tetrahydro-6-(phenylmethoxy)-4H-carbazol-4-oneYield 38.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

1,3-Cyclohexanedione (3.1 g) and the product of Stage (i) (5.6 g) in ethanol (196 ml) and water (39 ml) was stirred at room temperature for 3 h and then heated to reflux for 14 h. The resulting solution was allowed to cool, poured into water (500 ml) and the precipitate filtered and washed with isopropyl acetate and ether to give a solid. Recrystallisation from methanol gave the title compound as a solid (2.5 g) m.p. 235°-237°.

Workup

  1. temperatureheated
  2. temperatureto reflux for 14 h
  3. temperatureto cool
  4. filtrationthe precipitate filtered
  5. washwashed with isopropyl acetate and ether
  6. customto give a solid
  7. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-78fc489b6c4b4be39c7bb6d9b5564ba7
Source dataset
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04725615

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes