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

HRID 1297672ノート

反応式

HRID 1297672 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

HCID 585858466-Formyl-4-isobutyl-quinoline-3-carbonitrile収率 56%

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 6212Chloroform溶媒

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-1154d6301b674925ae73ea6e38ed6be2
出典データセット
uspto-grants-2007_07
特許番号
US07250515B2

反応ノート

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