Pyridine → 3'-fluoro-4'-hydroxyacetophenone-O-4-nitrobenzyloxime

HRID 41961노트

반응식

HRID 41961 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH3:10])[CH:5]=[CH:6][C:7]=1[OH:8].Cl.[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([CH2:20][O:21][NH2:22])=[CH:18][CH:17]=1)([O-:15])=[O:14].N1C=CC=CC=1>C(O)C>[N+:13]([C:16]1[CH:17]=[CH:18][C:19]([CH2:20][O:21][N:22]=[C:9]([C:4]2[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([F:1])[CH:3]=2)[CH3:10])=[CH:23][CH:24]=1)([O-:15])=[O:14]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 74967Hydroxylamine, O-((4-nitrophenyl)methyl)-, hydrochloride (1:1)HCID 27373251-(3-Fluoro-4-hydroxyphenyl)ethan-1-one

생성물 1

HCID 1363498393'-fluoro-4'-hydroxyacetophenone-O-4-nitrobenzyloxime

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 3′-fluoro-4′-hydroxyacetophenone (0.063 g, 0.411 mmol), O-(4-nitrobenzyl)hydroxylamine hydrochloride (0.100 g, 0.491 mmol) and pyridine (0.13 ml, 1.61 mmol) in ethanol (5 ml) was stirred at reflux under nitrogen for 5h and cooled to room temperature. The solution was concentrated to a pale yellow oil which was diluted with dichloromethane/water. The resultant mixture was extracted with dichloromethane (×3). The combined organic phases were washed with water and brine, dried over magnesium sulphate, filtered and concentrated to an off-white solid. The crude product was purified by column chromatography (SiO2), eluting with 8:2 petrol/ethyl acetate, to give a 3′-fluoro-4′-hydroxyacetophenone-O-4-nitrobenzyloxime (CP9-132) as light yellow solid (0.081 g, 65%),

후처리

  1. concentrationThe solution was concentrated to a pale yellow oil which
  2. additionwas diluted with dichloromethane/water
  3. extractionThe resultant mixture was extracted with dichloromethane (×3)
  4. washThe combined organic phases were washed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to an off-white solid
  8. customThe crude product was purified by column chromatography (SiO2)
  9. washeluting with 8:2 petrol/ethyl acetate

출처 및 근거

ORD 기록
ord-428838e03eb742dda3e73b743666b1ff
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536157B2

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