Hydrogen Peroxide → 3,5-dichloro-4-(2-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxoethyl)pyridine-N-oxide

HRID 1489683노트

반응식

HRID 1489683 반응식
[OH:1]O.[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:27])[C:9]=1[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:14]=1)=[O:12]>C(O)(=O)C.C(OCC)(=O)C>[Cl:27][C:8]1[CH:7]=[N+:6]([O-:1])[CH:5]=[C:4]([Cl:3])[C:9]=1[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:14]=1)=[O:12]

참가 물질

5

반응물 2

HCID 784Hydrogen Peroxide2회HCID 214695783-Cyclopentyloxy-4-methoxyphenyl 3,5-dichloropyrid-4-ylmethyl ketone

생성물 1

HCID 211878453,5-dichloro-4-(2-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxoethyl)pyridine-N-oxide

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

Aqueous 27.5% hydrogen peroxide (0.32 mL) is added to a solution of 3-cyclopentyloxy-4-methoxyphenyl 3,5-dichloropyrid-4-ylmethyl ketone (990 mg) in glacial acetic acid (13 mL). The reaction is heated at 80° C. for 8 hours then allowed to stand overnight at room temperature. A further aliquot of aqueous 27.5% hydrogen peroxide (0.32 mL) is added and the mixture heated at 80° C. for 2 hours. The reaction mixture is diluted with ethyl acetate (200 mL) and washed with saturated aqueous sodium bicarbonate until the washings remained basic. The mixture is washed with brine (50 mL), dried (MgSO4), concentrated and the residue recrystallized from a mixture of dichloromethane/ethyl acetate/heptane to give 3,5-dichloro-4-(2-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxoethyl)pyridine-N-oxide as a yellow solid, m.p. 179°-180° C. [Elemental analysis: C,57.3; H,4.81; N,3.54; Cl,18.0%; calculated for C19 H19Cl2NO4 : C,57.59; H,4.83; N,3.53; Cl, 17.89%.]

후처리

  1. temperaturethe mixture heated at 80° C. for 2 hours
  2. washwashed with saturated aqueous sodium bicarbonate until the washings
  3. washThe mixture is washed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customthe residue recrystallized from a mixture of dichloromethane/ethyl acetate/heptane

출처 및 근거

ORD 기록
ord-4023f70690294b76811598e454e3190e
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05679696

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