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

HRID 537093

反応式

HRID 537093 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 18681192Ethanol, mixt. with methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-899d5432338e466ca41209097754de76
出典データセット
uspto-grants-2014_10
特許番号
US08859773B2

関連ノート

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