Iodoethane → 1-Ethyl-7-fluoroindoline-2,3-dione

HRID 2114877Notes

Reaction equation

HRID 2114877 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].I[CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:14]([N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[F:1])[C:7](=[O:12])[C:8]1=[O:11])[CH3:15]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 5864187-Fluoroisatin

Product 1

HCID 692740961-Ethyl-7-fluoroindoline-2,3-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

7-Fluoro-1H-indole-2,3-dione (prepared according to the method of Gassman as described in U.S. Pat. No. 4,188,325 (4.00 g, 24.2 mmol), iodoethane (3.87 ml, 48.5 mmol) and potassium carbonate (6.61 g, 48.5 mmol) in DMF (20 ml) are stirred at room temperature for 20 hours. The reaction mixture is diluted with cold water and the resulting precipitate filtered and dried to give the title compound as an orange solid. HPLC r.t. 4.48 min; MS for C10H8FNO2 m/z 193.9 (M+H)+.

Workup

  1. filtrationthe resulting precipitate filtered
  2. customdried

Sources & evidence

ORD record
ord-48c4f2ed178347ee8f248cbbe5644e63
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

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