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

HRID 530333Notes

Reaction equation

HRID 530333 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 min before methyl iodide (0.18 g, 1.29 mmol) was added. After stirring for 2 h, the reaction mixture was treated with water, extracted with EtOAc, washed with water and brine in sequence, and dried over anhy. Na2SO4. After removal of the solvents under reduced pressure, the crude product (0.18 g, 80% yield) 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. customdried over anhy
  5. customAfter removal of the solvents under reduced pressure

Sources & evidence

ORD record
ord-d2c33c5ab35f418c9e7c0d6653b828ae
Source dataset
uspto-grants-2016_05
Patent number
US09353081B2

Reaction notes

Loading…