Ethyl 2-(3-nitropyridin-2-yl)oxyacetate → Ethyl [(3-amino-2-pyridinyl)oxy]acetate

HRID 1862332노트

반응식

HRID 1862332 반응식
[CH2:1]([O:3][C:4]([CH2:6][O:7][C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:5])[CH3:2]>[Pd].C(OCC)(=O)C>[NH2:14][C:13]1[C:8]([O:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[N:9][CH:10]=[CH:11][CH:12]=1

참가 물질

4

반응물 1

HCID 4425975Ethyl 2-(3-nitropyridin-2-yl)oxyacetate

생성물 1

HCID 18619191Ethyl [(3-amino-2-pyridinyl)oxy]acetate수율 88.5%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 48.3 g of 2-(ethoxycarbonyl)methoxy-3-nitropyridine, 7.8 g of 10% palladium/carbon and 540 ml of ethyl acetate was stirred for 3 hours at room temperature under hydrogen atmosphere. The reaction system was purged with nitrogen, then, the reaction solution was filtrated through Celite, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to obtain 37.1 g of 3-amino-2-(ethoxycarbonyl)methoxypyridine. 1H-NMR(CDCl3/300 MHz) δ(ppm): 1.27 (t, 3H, J=7.1 Hz), 3.8-3.9 (b, 2H), 4.24 (q, 2H, J=7.1 Hz), 4.93 (s, 2H), 6.7-6.8 (m, 1H), 6.8-7.0 (m, 1H), 7.4-7.6(m, 1H)

후처리

  1. customThe reaction system was purged with nitrogen
  2. filtrationthe reaction solution was filtrated through Celite
  3. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-67d09618b4604872b32e5d960810156f
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06537948B1

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