Acetic Anhydride → N-(6-chloro-2-methylpyridin-3-yl)acetamide

HRID 386025Notes

Reaction equation

HRID 386025 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:17](OC(=O)C)(=[O:19])[CH3:18]>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([NH:9][C:17](=[O:19])[CH3:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 70095003-Amino-6-chloro-2-picoline

Product 1

HCID 59525698N-(6-chloro-2-methylpyridin-3-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a dry flask, 6-chloro-2-methylpyridin-3-amine (200 mg, 1.40 mmol) and triethylamine (217 μl, 1.56 mmol) were taken up in dichloromethane (7.0 ml) under argon. The solution was cooled to 0° C. and stirred for 20 minutes. Acetic anhydride (134 μl, 1.42 mmol) was added dropwise over 15 minutes. The mixture was allowed to warm to room temperature and left to stir for 22 hours. The reaction was quenched with aqueous sodium bicarbonate and washed with ethyl acetate three times. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated. The resulting crude product was purified by silica gel chromatography (0-100% ethyl acetate/hexanes) to afford the title compound.

Workup

  1. temperatureto warm to room temperature
  2. waitleft
  3. stirringto stir for 22 hours
  4. customThe reaction was quenched with aqueous sodium bicarbonate
  5. washwashed with ethyl acetate three times
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting crude product was purified by silica gel chromatography (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-77a43f8ee84d4ed7b669d9fbc8456b4e
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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