Water → 7-Bromo-1,4,4-trimethyl-3,4-dihydroquinolin-2(1H)-one

HRID 2209293Notes

Reaction equation

HRID 2209293 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:14])([CH3:13])[CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[C:15]([O-])([O-])=O.[K+].[K+].IC.O>CN(C=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:14])([CH3:13])[CH2:7][C:8](=[O:12])[N:9]2[CH3:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 199637077-Bromo-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 199355167-Bromo-1,4,4-trimethyl-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-bromo-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one (210 mg, 0.83 mmol) and K2CO3 (335 mg, 2.42 mmol) were taken up in DMF (5 mL). Iodomethane (0.15 mL, 2.4 mmol) was added and the resulting mixture was stirred for 18 h. Water was added, and the resulting solids were filtered and washed with additional water to provide crude 7-bromo-1,4,4-trimethyl-3,4-dihydroquinolin-2(1H)-one that was used without further purification.

Workup

  1. filtrationthe resulting solids were filtered
  2. washwashed with additional water

Sources & evidence

ORD record
ord-219c66806e1645749a020632c3461177
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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