Water → 6-Bromo-8-fluoro-1-methyl-3,4-dihydroquinolin-2(1H)-one

HRID 1774839Notes

Reaction equation

HRID 1774839 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[NH:8][C:7](=[O:13])[CH2:6][CH2:5]2.[CH3:14]C(C)([O-])C.[K+].CI.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[N:8]([CH3:14])[C:7](=[O:13])[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 709774606-BROMO-8-FLUORO-3,4-DIHYDROQUINOLIN-2(1H)-ONE

Product 1

HCID 726988256-Bromo-8-fluoro-1-methyl-3,4-dihydroquinolin-2(1H)-oneYield 81.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-bromo-8-fluoro-3,4-dihydro-1H-quinolin-2-one (0.21 g, 0.86 mmol) in DMF (2 mL) was treated with potassium tert-butoxide (0.19 g, 1.72 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 30 minutes before methyl iodide (0.18 g, 1.29 mmol) was added. After stirring for 2 hours, the reaction mixture was treated with water, extracted with EtOAc, washed with water and brine in sequence, and dried over anhydrous Na2SO4. After removal of solvent under reduced pressure, the crude product (0.18 g, 80%) was obtained as a white solid. MS: 258.0 (M+H+)+.

Workup

  1. additionwas added
  2. extractionextracted with EtOAc
  3. washwashed with water and brine in sequence
  4. dry with materialdried over anhydrous Na2SO4
  5. customAfter removal of solvent under reduced pressure

Sources & evidence

ORD record
ord-817b0e83d1a04a3099d362fd23dde226
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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