2-甲酰基-3-氧代丙酸乙酯 → 1-(5-carboxy-2-methyl-phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 491851

反应方程式

HRID 491851 反应方程式
[CH2:1]([O:3][C:4](=[O:10])[CH:5]([CH:8]=O)[CH:6]=O)[CH3:2].Cl.[NH:12]([C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:17]([OH:19])=[O:18])[NH2:13]>CCO>[CH2:1]([O:3][C:4]([C:5]1[CH:8]=[N:13][N:12]([C:14]2[CH:15]=[C:16]([C:17]([OH:19])=[O:18])[CH:20]=[CH:21][C:22]=2[CH3:23])[CH:6]=1)=[O:10])[CH3:2]

参与物

4

反应物 2

HCID 110299552-甲酰基-3-氧代丙酸乙酯HCID 567775083-肼基-4-甲基苯甲酸盐酸盐

产物 1

HCID 575597081-(5-carboxy-2-methyl-phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester收率 68%

试剂、催化剂与溶剂 1

HCID 702乙醇溶剂2 次

实验过程

A solution of 2-formyl-3-oxo-propionic acid ethyl ester (S. H. Bertz et al., J. Org. Chem., 1982, 47, 2216) (1.44 g, 10 mmol) in EtOH (10 mL) was cooled in an ice bath. A slurry of 3-hydrazino-4-methyl-benzoic acid hydrochloride (2.02 g, 10 mmol) in EtOH (50 mL) was added and the reaction was stirred overnight. The EtOH was removed under reduced pressure and the residue partitioned between water and CH2Cl2. The layers were separated and the organic layer washed with brine. The organic layer was dried over Na2SO4, filtered, and concentrated. Hexanes were added and the solution concentrated. The resulting solid was collected by vacuum filtration, washed with hexanes and dried under vacuum to provide 1-(5-carboxy-2-methyl-phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester (1.86 g, 68%) as a yellow solid: ESI MS m/z 275 [C14H14N2O4+H]+.

后处理

  1. customThe EtOH was removed under reduced pressure
  2. customthe residue partitioned between water and CH2Cl2
  3. customThe layers were separated
  4. washthe organic layer washed with brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. additionHexanes were added
  9. concentrationthe solution concentrated
  10. filtrationThe resulting solid was collected by vacuum filtration
  11. washwashed with hexanes
  12. customdried under vacuum

来源与证据

ORD记录
ord-c22620a1782542e7943f04f163d8a864
来源数据集
uspto-grants-2009_05
专利号
US07531560B2

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