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

HRID 1862332ノート

反応式

HRID 1862332 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

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)

後処理

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

出典と根拠

ORDレコード
ord-67d09618b4604872b32e5d960810156f
出典データセット
uspto-grants-2003_03
特許番号
US06537948B1

反応ノート

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