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

HRID 515858

반응식

HRID 515858 반응식
[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

참가 물질

5

반응물 3

HCID 70602-MethylquinolineHCID 11430Potassium CarbonateHCID 11084032Triethylammonium formate

생성물 1

HCID 962892-Methyl-1,2,3,4-tetrahydroquinoline수율 102.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-20 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-c7b32f9d35df4118b14194b627fb80da
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108986B2

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