Dimethylformamide → 3,5-Dibromo-1,6-dimethylpyridin-2(1H)-one

HRID 1022229Notes

Reaction equation

HRID 1022229 reaction equation
[CH3:1]N(C=O)C.[Br:6][C:7]1[C:8](=[O:15])[NH:9][C:10]([CH3:14])=[C:11]([Br:13])[CH:12]=1.CI.C([O-])([O-])=O.[K+].[K+]>O>[Br:6][C:7]1[C:8](=[O:15])[N:9]([CH3:1])[C:10]([CH3:14])=[C:11]([Br:13])[CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2854813,5-Dibromo-6-methylpyridin-2-ol

Product 1

HCID 299237793,5-Dibromo-1,6-dimethylpyridin-2(1H)-oneYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with DMF (50 mL), 327c (10.0 g, 37.5 mmol), CH3I (5.3 g, 37.5 mmol), and K2CO3 (7.8 g, 56.2 mmol). The mixture was stirred at room temperature for 5 h. Water (100 mL) was added and the resulting white solid was collected to afford 327d (8.2 g, 78%) as a white solid. MS-ESI: [M+H]+ 280.

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customthe resulting white solid was collected

Sources & evidence

ORD record
ord-87732f30d1e4401f8ea12adb87488b8d
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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