Methyl quinoline-5-carboxylate → Methyl 5,6,7,8-tetrahydroquinoline-5-carboxylate

HRID 2175905Notes

Reaction equation

HRID 2175905 reaction equation
[N:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1>C(O)(C(F)(F)F)=O.[Pt]=O>[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 12503486Methyl quinoline-5-carboxylate

Product 1

HCID 77230270Methyl 5,6,7,8-tetrahydroquinoline-5-carboxylate

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

Methyl quinoline-5-carboxylate (3.67 g, 19.61 mmol) was dissolved in TFA (60 mL) and added platinum oxide (0.49 g, 2.16 mmol) then hydrogenated at room temperature overnight. The catalyst was filtered off and the filtrate was evaporated to dryness. The residue was chromatographed through a 120 g ISCO Redi-sep column and eluted with 5% of (10% NH4OH in MeOH) in DCM to yield methyl 5,6,7,8-tetrahydroquinoline-5-carboxylate: LC-MS: M+1=192.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated to dryness
  3. customThe residue was chromatographed through a 120 g ISCO Redi-sep column
  4. washeluted with 5% of (10% NH4OH in MeOH) in DCM

Sources & evidence

ORD record
ord-dbff58fd7fd348a78a6fd0c71d2b2075
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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