Acetic Anhydride → N-(5-Bromo-4-methylpyridin-2-yl)acetamide

HRID 2174953Notes

Reaction equation

HRID 2174953 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[C:10](OC(=O)C)(=[O:12])[CH3:11]>>[Br:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([NH:8][C:10](=[O:12])[CH3:11])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 8176952-Amino-5-bromo-4-methylpyridine

Product 1

HCID 15179563N-(5-Bromo-4-methylpyridin-2-yl)acetamide

Conditions

Temperature
110 °C

Procedure

5-bromo-4-methylpyridin-2-amine (0.578 mmol) was dissolved in acetic anhydride (5.78 mmol) and heated at 110° C. for 30 minutes. The reaction was quenched with ice. The aqueous reaction mixture neutralized with sodium hydroxide solution was extracted with ethyl acetate. The ethyl acetate layer was separated and dried over sodium sulfate. The organic layer was evaporated to dryness. The crude material was purified (silica column, MeOH/CHCl3). 1HNMR (300 MHz, DMSO-d6): 10.53 (s, 1H), 8.34 (s, 1H), 8.06 (s, 1H), 2.30 (s, 3H), 2.05 (s, 3H); MS (m/z): 231 (M+2)+.

Workup

  1. customThe reaction was quenched with ice
  2. extractionwas extracted with ethyl acetate
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried over sodium sulfate
  5. customThe organic layer was evaporated to dryness
  6. customThe crude material was purified (silica column, MeOH/CHCl3)

Sources & evidence

ORD record
ord-a86d8dbd4caf4356b0e29b047e6a0401
Source dataset
uspto-grants-2015_06
Patent number
US09062046B2

Reaction notes

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