Water → Methyl 1-(4-methylphenyl)-pyrazole-5-carboxylate

HRID 329339

반응식

HRID 329339 반응식
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([NH:7][NH2:8])=[CH:3][CH:2]=1.C(O[CH:13]=[CH:14][C:15](=O)[C:16]([O:18][CH3:19])=[O:17])C.O>C(O)(=O)C>[CH3:9][C:1]1[CH:6]=[CH:5][C:4]([N:7]2[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=[N:8]2)=[CH:3][CH:2]=1.[CH3:9][C:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[N:8]2)=[CH:3][CH:2]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 10875(4-Methylphenyl)hydrazineHCID 54443622Methyl 4-ethoxy-2-oxobut-3-enoat

생성물 2

HCID 14129278Methyl 1-(4-methylphenyl)-pyrazole-5-carboxylateHCID 14129279Methyl 1-(4-methylphenyl)-1H-pyrazole-3-carboxylate

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

반응 조건

온도
100 °C

실험 절차

12.5 g of p-tolylhydrazine in 150 ml of glacial acetic acid were added to a solution of 16 g of methyl 4-ethoxy-2-oxobut-3-enoat in 100 ml of glacial acetic acid at 50° C. The mixture was stirred at 100° C. for 5 hours, poured into 1 liter of water, and extracted twice with 100 ml of ethyl acetate. The organic phase was washed with saturated NaHCO3 solution and subsequently with water, and dried. After evaporating in a water-pump vaccum, the mixture was separated by distillation in a high vacuum. 4.1 g of methyl 1-(4-methylphenyl)-pyrazole-5-carboxylate of boiling point 116°-120° C./0.01 torr (example 8) and 5.3 g of methyl 1-(4-methylphenyl)-pyrazole-3-carboxylate of boiling point 138°-142° C./0.01 torr were obtained. The compounds were characterized by 1H NMR spectroscopy.

후처리

  1. extractionextracted twice with 100 ml of ethyl acetate
  2. washThe organic phase was washed with saturated NaHCO3 solution and subsequently with water
  3. customdried
  4. customAfter evaporating in a water-pump vaccum
  5. customthe mixture was separated by distillation in a high vacuum

출처 및 근거

ORD 기록
ord-e8f7fbe2e1b24b86bf2ee8929eb6660b
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04891057

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