4-Methylnicotinic acid → HCID 67068325, compound

HRID 1854353Notes

Reaction equation

HRID 1854353 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=1>CC(O)=O.[Pt](=O)=O>[C:8]([OH:10])(=[O:9])[CH3:7].[CH3:1][CH:2]1[CH2:3][CH2:4][NH:5][CH2:6][CH:7]1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 1

HCID 2291634-Methylnicotinic acid

Product 1

HCID 67068325HCID 67068325, compoundYield 195.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

4-Methylnicotinic acid (2.00 g, 14.6 mmol) and platinum(IV) oxide (0.30 g, 1.3 mmol) in AcOH (70 mL) were shaken under hydrogen at about 60 psi for about 3 days. The reaction was filtered through Celite® then concentrated under reduced pressure to afford 4-methylpiperidine-3-carboxylic acid acetate as an oil (2.9 g, 98%): LC/MS (Table 2, Method a) Rt=0.55 min; MS m/z: 144 (M+H)+.

Workup

  1. filtrationThe reaction was filtered through Celite®
  2. concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record
ord-3e02eb02d25e4de392ec08a9575f1d3f
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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