Triethylamine → 5-methyl-1-pyridin-4-yl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 220480

反応式

HRID 220480 の反応式
[CH2:1]([O:3][C:4](=[O:13])[C:5](=[CH:9]N(C)C)[C:6](=O)[CH3:7])[CH3:2].Cl.[N:15]1[CH:20]=[CH:19][C:18]([NH:21][NH2:22])=[CH:17][CH:16]=1.C(N(CC)CC)C>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[CH:9]=[N:22][N:21]([C:18]2[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=2)[C:6]=1[CH3:7])=[O:13])[CH3:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 3806790Ethyl 2-acetyl-3-(dimethylamino)acrylateHCID 223202584-Hydrazinylpyridine hydrochloride

生成物 1

HCID 222679435-methyl-1-pyridin-4-yl-1H-pyrazole-4-carboxylic acid ethyl ester収率 76%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Dissolve 2-dimethylaminomethylene-3-oxo-butyric acid ethyl ester (0.550 g, 2.96 mmol), pyridin-4-yl-hydrazine hydrochloride (0.454 g, 3.12 mmol) and triethylamine (0.435 mL, 3.12 mmol) in ethanol (12 mL) and reflux for 2 hr. Evaporate the mixture then dilute with saturated sodium bicarbonate and extract 3 times with ethyl acetate. Dry (sodium sulfate) the solution, filter and concentrate. Purify using silica gel chromatography, eluting with 50:50 ethyl acetate:hexane to give 5-methyl-1-pyridin-4-yl-1H-pyrazole-4-carboxylic acid ethyl ester as a tan solid (0.520 g, 76%). MS (ES): m/z=232 [M+H]+.

後処理

  1. temperaturereflux for 2 hr
  2. customEvaporate the mixture
  3. additionthen dilute with saturated sodium bicarbonate
  4. extractionextract 3 times with ethyl acetate
  5. dry with materialDry (sodium sulfate) the solution
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify
  9. washeluting with 50:50 ethyl acetate

出典と根拠

ORDレコード
ord-31bfe4e53cb547e89e123f0721c10505
出典データセット
uspto-grants-2012_06
特許番号
US08202873B2

関連ノート

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