Potassium Carbonate → Ethyl 5-amino-1-isopropyl-1H-pyrazole-4-carboxylate

HRID 537093

반응식

HRID 537093 반응식
[C:1]([C:3](=[CH:9]OCC)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].Cl.[CH:14]([NH:17][NH2:18])([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>C(O)C.CO>[NH2:2][C:1]1[N:17]([CH:14]([CH3:16])[CH3:15])[N:18]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 855731-Isopropylhydrazine hydrochloride

생성물 1

HCID 22762155Ethyl 5-amino-1-isopropyl-1H-pyrazole-4-carboxylate수율 94%

시약·촉매·용매 1

HCID 18681192Ethanol, mixt. with methanol용매

실험 절차

A mixture of ethyl 2-cyano-3-ethoxyacrylate (84.4 g, 0.50 mol), isopropyl hydrazine hydrochloride (55.2 g, 0.50 mol) and potassium carbonate (68.8 g, 0.50 mol) in 90% ethanol/methanol (1.5 L) was heated under reflux for 16 hours. The solvent was then removed in vacuo and water and ethyl acetate were added. The mixture was separated and the organic layer was dried over magnesium sulfate, filtered and the solvent was removed in vacuo to yield ethyl 5-amino-1-isopropyl-1H-pyrazole-4-carboxylate (92.4 g, 94%). +ESI (M+H) 198.1; 1H NMR (400 MHz, CDCl3, δ): 7.63 (s, 1H), 4.97 (br. s., 2H), 4.28 (q, 2H), 4.18 (m, 1H), 1.45 (d, 6H), 1.31 (t, 3H).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. customThe solvent was then removed in vacuo and water and ethyl acetate
  4. additionwere added
  5. customThe mixture was separated
  6. dry with materialthe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-899d5432338e466ca41209097754de76
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859773B2

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