Water → N-(2-chloropyridin-3-yl)acetamide

HRID 429515Notes

Reaction equation

HRID 429515 reaction equation
[Cl:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[C:16](Cl)(=[O:18])[CH3:17].O>ClCCl>[Cl:1][C:2]1[C:7]([NH:8][C:16](=[O:18])[CH3:17])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 805282-Chloro-3-pyridylamine

Product 1

HCID 4338791N-(2-chloropyridin-3-yl)acetamideYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2chloro-3-aminopyridine (51.4 g, 400 mmol) in dichloromethane (800 mL) at 0° C. was added triethylamine (31.0 mL, 440 mmol) followed by acetyl chloride (62.0 mL, 440 mmol). The reaction was allowed to warm to room temperature and was stirred overnight. The reaction mixture was poured into water (800 mL) and the layers were separated. The organic layer was treated with Darco™-G-60 (activated charcoal), heated to reflux, filtered over Celite™ (diatomaceous earth manufactured by Celite Corp., Santa Barbara, Calif.) and concentrated to an oil. The oil was crystallized in diisopropyl ether and the solids were filtered to afford 42.4 g (62% yield) of N-(2-chloro-pyridin-3-yl)-acetamide. M. p.=81-83° C. 1 NMR (400 MHz, CDCl3) δ2.23 (s, 3), 7.21 (dd, 1, J=8.1, 4.7) 7.67 (bs, 1), 8.06 (dd, 1, J=4.7, 1.3), δ8.66 (d, 1, J=7.9). 13C NMR (100 MHz, CDCl3) δ24.93, 123.34, 129.06, 131.89, 143.81, 144.08, 168.79.

Workup

  1. customthe layers were separated
  2. additionThe organic layer was treated with Darco™
  3. temperature(activated charcoal), heated
  4. temperatureto reflux
  5. filtrationfiltered over Celite™ (diatomaceous earth manufactured by Celite Corp., Santa Barbara, Calif.)
  6. concentrationconcentrated to an oil
  7. customThe oil was crystallized in diisopropyl ether
  8. filtrationthe solids were filtered

Sources & evidence

ORD record
ord-12da9f8a26924518b4a16dbdeab95fc6
Source dataset
uspto-grants-2001_11
Patent number
US06316632B1

Reaction notes

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