Dimethyl Sulfate → 6-Fluoro-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one

HRID 4375

Reaction equation

HRID 4375 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH2:7][C:6](=[O:15])[C:5]2=1.[C:16](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH3:16])[C:10]1[CH2:9][CH2:8][CH2:7][C:6](=[O:15])[C:5]2=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 3357046-fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-one

Product 1

HCID 201524556-Fluoro-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-oneYield 97.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The product of Stage (ii) (7.28 g), potassium carbonate (9.90 g), acetone (70 ml), and dimethylsulphate (5.1 ml) were vigorously stirred at room temperature overnight under nitrogen. The mixture was concentrated to one half of its volume and then stirred with water (350 ml) for 30 min. The mixture was filtered off, washed with water (50 ml), air-dried for 1 h, and dried in vacuo over phosphorus pentoxide to give the title compound as needles (7.59 g), m.p. 157.5°-158.5°.

Workup

  1. concentrationThe mixture was concentrated to one half of its volume
  2. filtrationThe mixture was filtered off
  3. washwashed with water (50 ml)
  4. customair-dried for 1 h
  5. dry with materialdried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-76b14a9408c64659932b886070897fcf
Source dataset
uspto-grants-1988_02
Patent number
US04725615

Linked notes

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