Water → Ethyl 2-(3-nitropyridin-2-yl)acetate

HRID 840924ノート

反応式

HRID 840924 の反応式
[N+:1]([C:4]1[C:5]([CH:10](C(OCC)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].O.[Cl-].[Li+]>CS(C)=O.[Cl-].[Na+].O>[N+:1]([C:4]1[C:5]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

参加物

6

反応物 3

HCID 962WaterHCID 433294Lithium Chloride2 回HCID 13147345Diethyl (3-nitropyridin-2-yl)propanedioate

生成物 1

HCID 10104538Ethyl 2-(3-nitropyridin-2-yl)acetate収率 92%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
100 °C

実験手順

Diethyl (3-nitropyridin-2-yl)-malonate (12.5 g, 0.044 mol) was dissolved in DMSO (150 mL) and water (0.79 mL, 0.044 mol) and lithium chloride (4.65 g, 0.11 mol) were added at room temperature under nitrogen. The reaction was warmed to 100° C. 12 hours and more lithium chloride (1 g) was added to the reaction. The reaction was heated for another 5 hours and cooled to room temperature. Brine (150 mL) was added to the reaction before extracting with EtOAc (3×, 275 mL each). The organics were combined and dried over sodium sulfate, then concentrated in vacuo. The resulting residue was triturated with diethyl ether and collected by filtration (8.6 g, 92% yield). 1H NMR 400 MHz (DMSO-d6) δ8.83 (m, 1H); 8.53 (m, 1H); 7.65 (m, 1H); 4.23 (s, 2H); 4.07 (m, 2H); 1.16 (m, 3H).

後処理

  1. temperatureThe reaction was heated for another 5 hours
  2. temperaturecooled to room temperature
  3. extractionbefore extracting with EtOAc (3×, 275 mL each)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was triturated with diethyl ether
  7. filtrationcollected by filtration (8.6 g, 92% yield)

出典と根拠

ORDレコード
ord-88502be674b042b2917c5a382a1fa380
出典データセット
uspto-grants-2002_04
特許番号
US06369086B1

反応ノート

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