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

HRID 515860Notes

Reaction equation

HRID 515860 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(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

4

Reactant 2

HCID 70602-MethylquinolineHCID 11084032Triethylammonium formate

Product 1

HCID 962892-Methyl-1,2,3,4-tetrahydroquinolineYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

In 60 ml of methylene chloride, 1.00 g of 2-methylquinoline was dissolved, and as a catalyst, 6.7 mg (0.2 mol %) of a crystalline (R)-chloro[(1,2,3,4,5-η)-pentamethyl-2,4-cyclopentadien-1-yl](2-pyrrolidinecarboxamidato-κN1, κN2)iridium(III) complex (Cp*Ir(Cl−)(R-PA-H+)) was added. After cooling to −10° C., 8.4 ml of a mixed solvent of formic acid/triethylamine (molar ratio: 5/2) was added dropwise, and the mixture was stirred at the same temperature for 2 days to give 2-methyl-1,2,3,4-tetrahydroquinoline (degree of conversion: 73%). The R-enantiomer was in excess and the optical purity was 90.2% ee.

Sources & evidence

ORD record
ord-e3feec3161f5419bb0579f07ffeb3f1e
Source dataset
uspto-grants-2015_08
Patent number
US09108986B2

Reaction notes

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