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

HRID 1774834Notes

Reaction equation

HRID 1774834 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 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) at 0° C. 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 stirred for 2 hours before water was added. After extraction of the reaction mixture with EtOAc, the organic layer was washed with water and brine in sequence. Then, it was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to give a crude product (0.49 g, 90%) 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. dry with materialThen, it was dried over anhydrous Na2SO4
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3be3bf3437ab4d629f6cf74ce3801838
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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