Acetic Acid → HCID 178468617、化合物

HRID 1093597

反応式

HRID 1093597 の反応式
[CH2:1]([O:3][C:4](=[O:16])[C:5](=O)[CH2:6][C:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].C(O)(=O)C.O.[NH2:22][NH2:23].C([O-])(O)=O.[Na+]>O>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:23][N:22]=1)=[O:16])[CH3:2]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 2265032,4-Dioxo-4-phenyl-butyric acid ethyl esterHCID 516892Sodium Bicarbonate

生成物 1

HCID 178468617HCID 178468617、化合物収率 88%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 2,4-dioxo-4-phenyl-butyric acid ethyl ester (1.68 g, 0.0076 mole), acetic acid (10 mL) and hydrazine hydrate (0.42 g, 0.0083 mole) was heated to reflux for 5 hours. The reaction mixture was then poured into iced water, basified with saturated aqueous NaHCO3 solution and the product was extracted with ethyl acetate. The ethyl acetate layer was collected and washed with brine solution, dried over sodium and concentrated under reduced pressure. The resulting residue was purified by column chromatography using basic aluminium oxide (50% ethyl acetate in hexane) to afford 1.442 g (88%) of 5-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester. LCMS: 217.09 (M+1)+, 97.92%. To a stirred solution of 5-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester (1.4 g, 0.00667 mol) in a mixture of THF (30 mL), methanol (15 mL) and H2O (10 mL) was added LiOH.H2O (0.839 g, 0.0199 mol) at ambient temperature. The resulting mixture was stirred at 45° C. overnight. Volatiles were evaporated and the residue was diluted with water, acidified with concentrated HCl solution and the product was extracted with ethyl acetate. The ethyl acetate layer was collected, dried over sodium sulfate and concentrated under reduced pressure to afford 1.26 g (86%) of 5-phenyl-1H-pyrazole-3-carboxylic acid. LCMS: 189.06 (M+1)+, 97.7%.

後処理

  1. temperatureto reflux for 5 hours
  2. extractionthe product was extracted with ethyl acetate
  3. customThe ethyl acetate layer was collected
  4. washwashed with brine solution
  5. dry with materialdried over sodium
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by column chromatography

出典と根拠

ORDレコード
ord-13b8d5ceb1d947f8bec300bdc587e6de
出典データセット
uspto-grants-2012_03
特許番号
US08129376B2

関連ノート

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