2-Methylquinoline → 2-Methyl-1,2,3,4-tetrahydroquinoline

HRID 515858

反応式

HRID 515858 の反応式
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(O)=O.C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

参加物

5

反応物 3

HCID 70602-MethylquinolineHCID 11430Potassium CarbonateHCID 11084032Triethylammonium formate

生成物 1

HCID 962892-Methyl-1,2,3,4-tetrahydroquinoline収率 102.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-20 °C

実験手順

In 60 ml of methylene chloride, 1.00 g of 2-methylquinoline was dissolved, and 66.5 mg (2.0 mol %) of crystalline (S)-chloro[(1,2,3,4,5-η)-pentamethyl-2,4-cyclopentadien-1-yl](2-pyrrolidinecarboxamidato-κN1, κN2)iridium(III) (Cp*Ir(Cl−)(S-PA-H+)) was added. After cooling to −20° C., 8.4 ml of a mixed solvent of formic acid/triethylamine (molar ratio: 5/2) was added dropwise, and the mixture was continuously stirred at the same temperature for 20 hours. Then, the reaction was completed. The reaction mixture was basified with an aqueous potassium carbonate solution and then the resulting layers were separated. The organic layer was washed with water and concentrated to give 1.05 g of 2-methyl-1,2,3,4-tetrahydroquinoline as an oil.

後処理

  1. customthe resulting layers were separated
  2. washThe organic layer was washed with water
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-c7b32f9d35df4118b14194b627fb80da
出典データセット
uspto-grants-2015_08
特許番号
US09108986B2

関連ノート

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