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

HRID 429515
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HRID 429515 반응식
[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
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-12da9f8a26924518b4a16dbdeab95fc6
출처 데이터셋
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06316632B1

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