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Hydrazine → 1H-Pyrazole-3-carboxylic acid, 5-ethyl-, ethyl ester

HRID 2283778
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HRID 2283778 반응식
O=[C:2]([CH2:8][C:9](=O)[CH2:10][CH3:11])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:13][NH2:14]>C(O)(=O)C>[CH2:10]([C:9]1[NH:14][N:13]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:8]=1)[CH3:11]
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참가 물질

4

반응물 2

HCID 9321HydrazineHCID 61590Ethyl-2,4-dioxohexanoate

생성물 1

HCID 80276141H-Pyrazole-3-carboxylic acid, 5-ethyl-, ethyl ester수율 57.7%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A solution of ethyl 2,4-dioxohexanoate (˜0.464 mol), prepared as described in Part A of Example 10, in glacial acetic acid (300 mL) was cooled to 0° C. Hydrazine (8.91 g, 0.278 mol) was added dropwise. The reaction was allowed to warm to ambient temperature, stirred overnight, and concentrated under reduced pressure. The residue was adjusted to pH 10 with the addition of 2 M aqueous sodium carbonate. The mixture was extracted with chloroform (3×250 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 27.0 g of ethyl 5-ethyl-1H-pyrazole-3-carboxylate, which was used without purification.

후처리

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was adjusted to pH 10 with the addition of 2 M aqueous sodium carbonate
  3. extractionThe mixture was extracted with chloroform (3×250 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-79612d42754647129f3e3ed88ccd2584
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09145410B2

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