Acetic Anhydride → N-(2-Methylpyridin-3-yl)acetamide

HRID 1094460Notes

Reaction equation

HRID 1094460 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9]1[C:10]([CH3:15])=[N:11][CH:12]=[CH:13][CH:14]=1.C(N(C(C)C)CC)(C)C>ClCCl>[CH3:15][C:10]1[C:9]([NH:8][C:5](=[O:7])[CH3:6])=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 5726163-Amino-2-methylpyridine

Product 1

HCID 23070203N-(2-Methylpyridin-3-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Acetic Acid Anhydride (17.9 mmol; 1.7 mL) was added to 3-Amino-2-picoline (17.0 mmol; 1.8 g) in dichloromethane (10 mL) and diisopropylethylamine (17.9 mmol; 3.1 mL) at 25° C. under argon. The reaction aged 30 min at 25° C. then was diluted with dichloromethane and extracted with water and brine. The aqueous layer was extracted with dichloromethane and ether then the combined organics were dried over sodium sulfate, filtered and concentrated in vacuo. The resulting yellow oil was purified by chromatography (0% to 66% ethyl acetate in hexane) to afford the title compound.

Workup

  1. extractionextracted with water and brine
  2. extractionThe aqueous layer was extracted with dichloromethane and ether
  3. dry with materialthe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting yellow oil was purified by chromatography (0% to 66% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c2e2195a99ff4f518fa151e6b2f75258
Source dataset
uspto-grants-2012_03
Patent number
US08133907B2

Reaction notes

Loading…