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

HRID 37497

반응식

HRID 37497 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e1042bcf07c04ef68cc62404a8ba4b14
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420275

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