(2-Phenylquinolin-7-yl)methanol → 7-Methyl-2-phenylquinoline

HRID 244082

反応式

HRID 244082 の反応式
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][C:11]([CH:17]=O)=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C2C=CC3C(=CC(CO)=CC=3)N=2)C=CC=CC=1>C(Cl)(Cl)Cl.O=[Mn]=O>[CH3:17][C:11]1[CH:10]=[C:9]2[C:14]([CH:15]=[CH:16][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8]2)=[CH:13][CH:12]=1

参加物

5

反応物 2

HCID 22062823(2-Phenylquinolin-7-yl)methanolHCID 468355462-Phenylquinoline-7-carbaldehyde

生成物 1

HCID 2877157-Methyl-2-phenylquinoline

試薬・触媒・溶媒 2

HCID 14801Manganese dioxide触媒HCID 6212Chloroform溶媒

実験手順

Additionally, 2-phenylquinoline-7-carbaldehyde could be prepared as follows: To a solution of (2-phenylquinolin-7-yl)methanol (75 mg, 0.319 mmol) in chloroform (1 mL) was added MnO2 (277 mg, 3.19 mmol). The mixture was stirred at rt for 20 h and filtered through a Celite pad. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (1% MeOH in dichloromethane) to afford the title compound. 1H-NMR (CDCl3, 400 MHz) δ 7.50-7.59 (m, 3H), 7.95 (d, J=8.8 Hz, 1H), 8.04 (dd, J=2.4, 8.8 Hz, 2H), 8.19-8.22 (m, 2H), 8.31 (d, J=8.8 Hz, 1H), 8.69 (s, 1H), 10.26 (s, 1H). MS (ES+): m/z 234 [MH+]. HPLC: tR=3.59 min (OpenLynx, polar—5 min).

後処理

  1. filtrationfiltered through a Celite pad
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (1% MeOH in dichloromethane)

出典と根拠

ORDレコード
ord-7266d67c0ae94cfa9fd667485130f3a1
出典データセット
uspto-grants-2014_02
特許番号
US08653268B2

関連ノート

読み込み中…