HCID 3265055, compound → 8-Fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-one

HRID 1723291Notes

Reaction equation

HRID 1723291 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[CH:10]=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[NH:8][C:9]1[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[C:10]2=1

Participants

5

Reactant 1

HCID 3265055HCID 3265055, compound

Product 1

HCID 221477458-Fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-oneYield 68.9%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

3-[(2-Fluorophenyl)amino]-2-cyclohexen-1-one (14.8 g), palladium (II) acetate (1 g), and copper (II) acetate (29.5 g) were heated together in DMF (100 ml) under nitrogen at 140° for 2 h. The solvent was removed in vacuo, and the residue was purified by FCC eluting with ether to give the title compound (10.1 g), m.p. 222°-224°.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by FCC
  3. washeluting with ether

Sources & evidence

ORD record
ord-d58e7cb8142f4c1b97a750f860f15eae
Source dataset
uspto-grants-1989_08
Patent number
US04859662

Reaction notes

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