Methyl quinoline-7-carboxylate → Methyl 1,2,3,4-tetrahydroquinoline-7-carboxylate

HRID 349031

Reaction equation

HRID 349031 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1>CO.O=[Pt]=O>[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 12554532Methyl quinoline-7-carboxylate

Product 1

HCID 16244389Methyl 1,2,3,4-tetrahydroquinoline-7-carboxylateYield 98.8%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl quinoline-7-carboxylate (185 mg, 1.0 mmol) and PtO2 (20 mg) in methanol (10 mL) was shaken under an atmosphere of hydrogen for 2 h. The reaction mixture was filtered through diatomaceous earth, and concentrated under reduced pressure to provide methyl 1,2,3,4-tetrahydroquinoline-7-carboxylate (189 mg): ESI MS m/z 192 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-02acc3f835484419afed0281129fcee5
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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