HCID 20446660, compound → HCID 20446656, compound

HRID 326139Notes

Reaction equation

HRID 326139 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5][N:4]=1)#[N:2]>CO.[Pd]>[NH2:2][CH2:1][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 1

HCID 20446660HCID 20446660, compound

Product 1

HCID 20446656HCID 20446656, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Cyano-4-(3-methoxycarbonylpropyl)pyridine (0.83 g) is hydrogenated at 3 atmospheres for 3 hours in 9 ml of methanol with 0.4 g of 10% palladium on charcoal. Filtration, evaporation, and preparative thin layer chromatography on silica gel with 1:1 methanol-ethyl acetate yields 2-aminomethyl-4-(3-methoxycarbonylpropyl)pyridine; Rf, 0.37 (EtOAc-MeOH 1:1, 1% NH4OH); NMR (CDCl3) 3.67 (s, 3 H), 4.15 (s, 2 H).

Workup

  1. filtrationFiltration, evaporation, and preparative thin layer chromatography on silica gel with 1:1 methanol-ethyl acetate

Sources & evidence

ORD record
ord-fdb21d6f297b4e298d95edcbc88720c6
Source dataset
uspto-grants-1984_04
Patent number
US04444775

Reaction notes

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