2-Fluoroaniline → 1-Acetyl-2-methyl-4-[(2-fluorophenyl)imino]-1,2,3,4-tetrahydroquinoline

HRID 2167239

反応式

HRID 2167239 の反応式
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=O)[CH2:6][CH:5]1[CH3:15])(=[O:3])[CH3:2].[F:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19]>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[N:19][C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[F:16])[CH2:6][CH:5]1[CH3:15])(=[O:3])[CH3:2]

参加物

5

反応物 2

HCID 95842-FluoroanilineHCID 5895634(1H)-Quinolinone, 1-acetyl-2,3-dihydro-2-methyl-

生成物 1

HCID 666252411-Acetyl-2-methyl-4-[(2-fluorophenyl)imino]-1,2,3,4-tetrahydroquinoline収率 82.3%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 1140Toluene溶媒

実験手順

[Step 1] 50 mg of 1-acetyl-4-oxo-2-methyl-1,2,3,4-tetrahydroquinoline and 83 mg of 2-fluoroaniline were dissolved in 2 mL of toluene, and 125 μL of titanium tetrachloride (1.0 M dichloromethane solution) was added to the solution under ice cooling. The resulting mixture was stirred for one hour under ice cooling, and then was stirred for 3 hours at 80° C. After completion of the reaction, the reaction liquid was filtered through Celite and was concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (diethyl ether:hexane=2:1), and thus 60 mg (81%) of 1-acetyl-2-methyl-4-[(2-fluorophenyl)imino]-1,2,3,4-tetrahy droquinoline was obtained as a yellow oily substance.

後処理

  1. stirringwas stirred for 3 hours at 80° C
  2. customAfter completion of the reaction
  3. customthe reaction liquid
  4. filtrationwas filtered through Celite
  5. concentrationwas concentrated under reduced pressure
  6. customThe resulting residue was purified

出典と根拠

ORDレコード
ord-53075a29a7834672bc889afd392c3c78
出典データセット
uspto-grants-2015_06
特許番号
US09045423B2

関連ノート

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