Dimethylformamide → 2-Chloro-3,4-diethoxycarbonyl-5-nitro-6-phenylpyridine

HRID 37497

反応式

HRID 37497 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:7](=O)[NH:8][C:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:10]([N+:17]([O-:19])=[O:18])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:5])[CH3:2].CN(C=O)C.P(Cl)(Cl)([Cl:34])=O>>[Cl:34][C:7]1[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]([N+:17]([O-:19])=[O:18])=[C:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:8]=1

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 19935597Diethyl 2-hydroxy-5-nitro-6-phenylpyridine-3,4-dicarboxylate

生成物 1

HCID 199355872-Chloro-3,4-diethoxycarbonyl-5-nitro-6-phenylpyridine

反応条件

温度
100 °C

実験手順

In 6.5 ml of phosphorus oxychloride was dissolved 2.5 g of 3,4-diethoxycarbonyl-5-nitro-6-phenyl-2pyridone, followed by addition of 1 ml of DMF. The mixture was heated at 100° C. for 30 minutes. After the reaction mixture was concentrated under reduced pressure, an aqueous solution of sodium hydrogencarbonate was added to the residue for neutralization, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After the solvent was distilled off, the residue was subjected to silica gel column chromatography (eluent:ethyl acetate/hexane 1:2), to give 1.9 g of the title compound as yellow needles.

後処理

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. additionan aqueous solution of sodium hydrogencarbonate was added to the residue for neutralization
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride and dried over magnesium sulfate
  6. distillationAfter the solvent was distilled off

出典と根拠

ORDレコード
ord-e1042bcf07c04ef68cc62404a8ba4b14
出典データセット
uspto-grants-1995_05
特許番号
US05420275

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