Tert-butyl 4-cyanobenzoate → 4-(Amino-hydroxyimino)methylbenzoic acid t-butyl ester

HRID 1417186노트

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HRID 1417186 반응식
[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:17][OH:18].C(=O)([O-])O.[Na+]>C(O)(C)(C)C.O>[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:8]=[CH:9][C:10]([CH:13]=[N:14][O:18][NH2:17])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 271408Tert-butyl 4-cyanobenzoateHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

생성물 1

HCID 544161174-(Amino-hydroxyimino)methylbenzoic acid t-butyl ester수율 88.2%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6386tert-Butanol용매

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온도
80 °C

실험 절차

In a mixture of 21.2 ml of t-butanol and 2.1 ml of water were dissolved 4.3 g of 4-cyanobenzoic t-butyl ester, 1.84 g of hydroxylamine hydrochloride and 2.31 g of sodium hydrogen carbonate. The solution was stirred for 2 hours at 80° C. To the reaction mixture was added water, and the mixture was subjected to extraction with ethyl acetate. The organic layer was concentrated under reduced pressure. The concentrate was purified by means of silica gel column chromatography (hexane/ethyl acetate=1/1), followed by crystallization from hexane to afford 4.41 g of the title compound as colorless needles.

후처리

  1. extractionthe mixture was subjected to extraction with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customThe concentrate was purified by means of silica gel column chromatography (hexane/ethyl acetate=1/1)
  4. customfollowed by crystallization from hexane

출처 및 근거

ORD 기록
ord-4a6c9e1932b6473386e78a32bd79f87d
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05876756

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