Hydrazine hydrate (1:1) → 5-Chloro-2-phenylpentanoic acid hydrazide

HRID 1009453

반응식

HRID 1009453 반응식
O.[NH2:2][NH2:3].[Cl:4][CH2:5][CH2:6][CH2:7][CH:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9](OC)=[O:10]>C(O)C>[Cl:4][CH2:5][CH2:6][CH2:7][CH:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9]([NH:2][NH2:3])=[O:10]

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 67067286Methyl 5-chloro-2-phenylpentanoate

생성물 1

HCID 668392255-Chloro-2-phenylpentanoic acid hydrazide

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of methyl phenylacetate (2.0 g) in DMF (5 mL) was added to a solution of sodium hydride (containing mineral oil at 40%, 590 mg) in DMF (20 mL) under ice-cooling. The reaction solution was stirred for 10 minutes, further stirred at room temperature for 30 minutes and then ice-cooled again. A solution of 1-chloro-3-iodopropane (2.99 g) in DMF (5 mL) was added to the reaction mixture, and the reaction solution was stirred at room temperature overnight. Water and ethyl acetate were added to the reaction mixture, and the organic layer was separated. The resulting organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain a crude product of methyl 5-chloro-2-phenylpentanoate. Hydrazine monohydrate (8 mL) was added to a solution of the resulting crude methyl 5-chloro-2-phenylpentanoate (3.279 g) in ethanol (20 mL), and the reaction solution was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure. Saturated sodium bicarbonate water and ethyl acetate and were added to the residue, and the organic layer was separated. The resulting organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 730 mg of the title compound. The property values of the compound are as follows.

후처리

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionSaturated sodium bicarbonate water and ethyl acetate and were added to the residue
  3. customthe organic layer was separated
  4. washThe resulting organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

출처 및 근거

ORD 기록
ord-70d59976087a4fb1b1b514424bde0a32
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973033B2

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