Methyl iodide → 7-Fluoro-1-methylindoline-2,3-dione

HRID 2114863Notes

Reaction equation

HRID 2114863 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[C:7]2=[O:12].IC.[C:15](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:15])[C:8](=[O:11])[C:7]2=[O:12]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5864187-Fluoroisatin

Product 1

HCID 118459677-Fluoro-1-methylindoline-2,3-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

7-Fluoro-1H-indole-2,3-dione (5, prepared according to the method of Gassman as described in U.S. Pat. No. 4,188,325, 3.00 g, 0.182 mol), iodomethane (3.40 ml, 0.545 mol) and potassium carbonate (4.92 g, 0.0363 mol) in DMF (15 ml) are stirred at room temperature for 1 hour. The reaction mixture is diluted with cold water and the resulting precipitate filtered and dried to give the title compound as a solid. HPLC r.t. 4.01 min; MS for C9H6FNO2 m/z 180.0 (M+H)+.

Workup

  1. filtrationthe resulting precipitate filtered
  2. customdried

Sources & evidence

ORD record
ord-89470784ae1f45628126e5c3981a3ab7
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

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