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

HRID 515858

Reaction equation

HRID 515858 reaction equation
[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

Participants

5

Reactant 3

HCID 70602-MethylquinolineHCID 11430Potassium CarbonateHCID 11084032Triethylammonium formate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-c7b32f9d35df4118b14194b627fb80da
Source dataset
uspto-grants-2015_08
Patent number
US09108986B2

Linked notes

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