Cornforth reagent → N,N-diethyl-4-(8-quinolinecarbonyl)benzamide

HRID 30499

反応式

HRID 30499 の反応式
[CH2:1]([N:3]([CH2:24][CH3:25])[C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:22])[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)=[CH:7][CH:6]=1)[CH3:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl.CCCCCCC>[CH2:24]([N:3]([CH2:1][CH3:2])[C:4](=[O:23])[C:5]1[CH:6]=[CH:7][C:8]([C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)=[O:22])=[CH:9][CH:10]=1)[CH3:25]

参加物

5

反応物 2

HCID 2724130Cornforth reagent2 回HCID 10711782N,N-diethyl-4-[hydroxy(8-quinolinyl)methyl]benzamide

生成物 1

HCID 22145457N,N-diethyl-4-(8-quinolinecarbonyl)benzamide収率 60.2%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8900Heptane溶媒

実験手順

16 (3.0 g, 9.0 mmol) was dissolved in CH2Cl2 (25 mL) and powdered pyridinium dichromate (PDC) (5.0 g, 13 mmol) was added portionwise at 25° C. Two more portions of PDC (0.5 g) were added after 3 h and 12 h. After 24 h, the solution was diluted with heptane and filtered through silica gel. Eluton with EtOAc and evaporation in vacuo gave 17 (1.8 g, 60%). MS: 332, 303, 275, 260, 232, 204, 176, 156, 128, 115. 1H NMR (CDCl3): δ1.1, 1.3 (2m, 6H), 3.22, 3.55 (2m, 4H), 7.39 (d, J=8 Hz, 2H), 7.43 (m, 1H), 7.65 (m, 1H), 7.75 (m, 1H), 7.86 (d, J=8 Hz, 2H), 7.98 (m, 1H), 8.23 (m, 1H), 8.83 (m, 2H).

後処理

  1. filtrationfiltered through silica gel
  2. customEluton with EtOAc and evaporation in vacuo

出典と根拠

ORDレコード
ord-912e2ddd3624430188b9f5b24f5b3db8
出典データセット
uspto-grants-2008_09
特許番号
US07423154B2

関連ノート

読み込み中…