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Water → 1,2,3,9-Tetrahydro-6-methoxy-9-methyl-4H-carbazol-4-one

HRID 4380
Notes
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Reaction equation

HRID 4380 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH2:16][CH2:15][CH2:14][C:13](=[O:22])[C:12]2=1.S(OC)(OC)(=O)=O.O>CC(C)=O>[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[N:18]([CH3:1])[C:17]1[CH2:16][CH2:15][CH2:14][C:13](=[O:22])[C:12]2=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 152128016-Methoxy-1,2,3,9-tetrahydro-4H-carbazol-4-one

Product 1

HCID 197698301,2,3,9-Tetrahydro-6-methoxy-9-methyl-4H-carbazol-4-oneYield 78.2%

Reagents, catalysts & solvents 1

HCID 180
Acetone
Solvent

Procedure

Anhydrous potassium carbonate (2.24 g) was added to a solution of the product of Stage (i) (3 g) in acetone (30 ml) at room temperature and stirred for 30 min. Dimethyl sulphate (1.6 ml) was added and the mixture was heated to reflux for 4 h. The resulting solution was poured into water (150 ml) and the resulting precipitate filtered off to give the title compound as a solid (2.5 g), m.p. 150°-151°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 h
  3. filtrationthe resulting precipitate filtered off

Sources & evidence

ORD record
ord-1ac4895b46ac455b903ac181d0e5e30d
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