Water → 6-Bromo-8-chloro-1-methyl-1,2,3,4-tetrahydroquinolin-2-one

HRID 1774843Notes

Reaction equation

HRID 1774843 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl: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]([Cl: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 709797726-Bromo-8-chloro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 722082846-Bromo-8-chloro-1-methyl-1,2,3,4-tetrahydroquinolin-2-oneYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-bromo-8-chloro-3,4-dihydro-1H-quinolin-2-one (7.0 g, 26.9 mmol) in DMF (100 mL) was treated with potassium tert-butoxide (6.0 g, 53.8 mmol) at 0° C. portionwise. The resulting mixture was stirred at 0° C. for 30 minutes before methyl iodide (5.0 g, 35.0 mmol) was added. After stirred for 12 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 (3.3 g, 45%) was obtained as a white solid.

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-a2ef4ba7dac3402da01744e0d06b57f5
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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