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

HRID 1168233ノート

反応式

HRID 1168233 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 93%

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. for 12 h, 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, and the reaction mixture was extracted with EtOAc (3×275 mL). The extracts were combined, dried over sodium sulfate and concentrated in vacuo. The resulting residue was triturated with diethyl ether and collected by filtration to yield the title compound (8.6 g, 92% yield). 1H NMR 400 MHz (DMSO-d6): δ 8.83 (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. extractionthe reaction mixture was extracted with EtOAc (3×275 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was triturated with diethyl ether
  7. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-f2557ca1194e49178bf5b91eef639777
出典データセット
uspto-grants-2003_09
特許番号
US06624171B1

反応ノート

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