Methanol → 1-(2-Methyl-pyridin-4-yl)-ethanone oxime

HRID 2108384노트

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HRID 2108384 반응식
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([CH3:10])[CH:5]=1)(=O)[CH3:2].Cl.[NH2:12][OH:13].CO.O.O.O.C([O-])(=O)C.[Na+]>O.[Cl-].[Na+].O>[CH3:10][C:6]1[CH:5]=[C:4]([C:1](=[N:12][OH:13])[CH3:2])[CH:9]=[CH:8][N:7]=1

참가 물질

7

반응물 4

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 207050141-(2-Methylpyridin-4-yl)ethan-1-oneHCID 23665404Sodium Acetate Trihydrate

생성물 1

HCID 1363592001-(2-Methyl-pyridin-4-yl)-ethanone oxime수율 67%

시약·촉매·용매 2

HCID 962Water용매2회HCID 57417360Sodium chloride; water용매

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온도
70 °C

실험 절차

To a stirred suspension of 4-acetyl-2-methyl-pyridine [CAS No. 2732-28-7] (9.7 g, 71.8 mmol) in water (115 ml) was added at room temperature hydroxylamine hydrochloride (8.48 g, 122 mmol) and the mixture was heated to 70° C. At this temperature methanol (145 ml) was added dropwise over a period of 15 min and afterwards a solution of sodium acetate trihydrate (25.4 g, 187 mmol) in water (115 ml) was added dropwise over a period of 15 min. The reaction mixture was stirred at 80° C. for 3.5 h, brine (150 ml) was added and the solution was extracted with ethyl acetate (2×250 ml). The combined organic layers were washed with brine (150 ml), dried (MgSO4) and evaporated. The crude product was purified by crystallization from ethyl acetate/hexane to give 1-(2-methyl-pyridin-4-yl)-ethanone oxime (7.25 g, 67%) as an off-white solid; mp 154° C.

후처리

  1. extractionthe solution was extracted with ethyl acetate (2×250 ml)
  2. washThe combined organic layers were washed with brine (150 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was purified by crystallization from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-b77cabe33af04792a1dd03c65ea168da
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514443B2

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