Water → 2-Acetylamino-5-bromo-3-methylpyridine

HRID 2287594Notes

Reaction equation

HRID 2287594 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[C:10](Cl)(=[O:12])[CH3:11].O>CN(C)C1C=CC=CC=1>[C:10]([NH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 1379342-Amino-5-bromo-3-methylpyridine

Product 1

HCID 9019482-Acetylamino-5-bromo-3-methylpyridineYield 32.7%

Reagents, catalysts & solvents 1

HCID 949N,N-DimethylanilineSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-amino-5-bromo-3-methylpyridine (300 mg) in N,N-dimethylaniline (486 mg) was added acetyl chloride (138 mg), and the mixture was stirred for 3 hours at 70° C. The reaction mixture was poured into water, and extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform) to give 2-acetamido-5-bromo-3-methylpyridine (120 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-957a8b1fcb38401cac226cb2a64ace95
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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