6-Hydroxymethyl-4-isobutyl-1,4-dihydro-quinoline-3-carbonitrile → 6-Formyl-4-isobutyl-quinoline-3-carbonitrile

HRID 1297672노트

반응식

HRID 1297672 반응식
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]([C:13]#[N:14])[CH:6]2[CH2:15][CH:16]([CH3:18])[CH3:17]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([C:13]#[N:14])=[C:6]2[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:1]

참가 물질

4

반응물 1

HCID 585857716-Hydroxymethyl-4-isobutyl-1,4-dihydro-quinoline-3-carbonitrile

생성물 1

HCID 585858466-Formyl-4-isobutyl-quinoline-3-carbonitrile수율 56%

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 6212Chloroform용매

실험 절차

To the solution of 6-hydroxymethyl-4-isobutyl-1,4-dihydro-quinoline-3-carbonitrile (200 mg, 0.83 mmol) in chloroform (6 mL) was added manganese dioxide (300 mg). The mixture was stirred at reflux for 10 h. After removal of the solid by filtration, the filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 0%-30% ethyl acetate in hexanes in 30 min) afforded 6-formyl-4-isobutyl-quinoline-3-carbonitrile (110 mg, 56%) as a white solid. LC-MS m/e 239 (MH+).

후처리

  1. temperatureat reflux for 10 h
  2. customAfter removal of the solid
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-1154d6301b674925ae73ea6e38ed6be2
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07250515B2

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