Water → 2-N-methyl-6-fluoro-1-isoquinolinone

HRID 518282

Reaction equation

HRID 518282 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[NH:9][CH:8]=[CH:7]2.[CH3:15]I.O>CN(C=O)C.C(OCC)(=O)C>[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[N:9]([CH3:15])[CH:8]=[CH:7]2

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 450908026-Fluoroisoquinolin-1(2H)-one

Product 1

HCID 693999762-N-methyl-6-fluoro-1-isoquinolinoneYield 107.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Sodium hydride (60% in mineral oil) (211 mg, 5.27 mmol) was added to 6-fluoro-1,2-dihydroisoquinolin-1-one (716 mg, 4.39 mmol) in anhydrous DMF (6 mL) cooled in an ice bath. The mixture was stirred for about 30 min at room temperature and methyl iodide (0.328 mL, 5.27 mmol) was added dropwise. After 1 h, the reaction was judged to be about 60% complete and additional methyl iodide (0.2 mL, 3.2 mmol) was added. After about 1 h, ice and water and ethyl acetate were added to the mixture. After extractive work up with ethyl acetate, the title compound (836 mg) was obtained as a cream solid and carried on without purification.

Workup

  1. temperaturecooled in an ice bath
  2. waitAfter 1 h
  3. waitAfter about 1 h

Sources & evidence

ORD record
ord-eb373744b1ed4cd9aa8d85a5a2f98cc3
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Linked notes

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