Water → N-[4-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)phenyl]benzamide

HRID 1291614ノート

反応式

HRID 1291614 の反応式
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>ClCCl>[C:27]([NH:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

参加物

6

反応物 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 2984117(4-aminophenyl)(3,4-dihydroquinolin-1(2H)-yl)methanone

生成物 1

HCID 10642000N-[4-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)phenyl]benzamide収率 34.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1-(4-aminobenzoyl)-1,2,3,4-tetrahydroquinoline (0.5 g) in dichloromethane (20 ml) is added triethylamine (0.3 g), and thereto is added benzoyl chloride (0.28 g) under ice-cooling. The mixture is stirred at room temperature for 1 hour. To the reaction mixture is added water and extracted with dichloromethane. The extract is dried over magnesium sulfate and the solvent is distilled off under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=50:1) and recrystallized from methanol to give 1-[4-(benzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (245 mg) as white powder, m.p. 202.5°-203.5° C.

後処理

  1. temperaturecooling
  2. extractionextracted with dichloromethane
  3. dry with materialThe extract is dried over magnesium sulfate
  4. distillationthe solvent is distilled off under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=50:1)
  6. customrecrystallized from methanol

出典と根拠

ORDレコード
ord-dcaa42da209b4948a9e6fbfa38b792b1
出典データセット
uspto-grants-1998_05
特許番号
US05753677

反応ノート

読み込み中…