Water → 6-Bromo-7-chloro-1-methyl-3,4-dihydro-1H-quinolin-2-one

HRID 530341Notes

Reaction equation

HRID 530341 reaction equation
[CH3:1]C(C)([O-])C.[K+].[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[Cl:18])[NH:14][C:13](=[O:19])[CH2:12][CH2:11]2.CI.O>CN(C=O)C>[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[Cl:18])[N:14]([CH3:1])[C:13](=[O:19])[CH2:12][CH2:11]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 709793626-Bromo-7-chloro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 866791856-Bromo-7-chloro-1-methyl-3,4-dihydro-1H-quinolin-2-oneYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Potassium tert-butoxide (0.45 g, 4.0 mmol) was added at 0° C. to a solution of 6-bromo-7-chloro-3,4-dihydro-1H-quinolin-2-one (0.52 g, 2.0 mmol) in DMF (5 mL). Then, the reaction mixture was stirred at 0° C. for 30 min and methyl iodide (0.18 g, 1.29 mmol) was added. The resulting mixture was then stirred for 2 h before water was added. After extraction of the reaction mixture with EtOAc, the organic layer was washed with water and brine in sequence. Then, the organic layer was dried over anhy. Na2SO4 and the solvent was removed under reduced pressure to give a crude product (0.49 g, 90% yield) as a white solid. MS: 274.0 (M+H)+.

Workup

  1. additionwas added
  2. extractionAfter extraction of the reaction mixture with EtOAc
  3. washthe organic layer was washed with water and brine in sequence
  4. customThen, the organic layer was dried over anhy
  5. customNa2SO4 and the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f6e132b9dd544c1089f5a6d221a3a916
Source dataset
uspto-grants-2016_05
Patent number
US09353081B2

Reaction notes

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