Hydrochloric Acid → 2-Aminomethyl-3-(ethoxycarbonylmethoxy)pyridine dihydrochloride

HRID 1271552Notes

Reaction equation

HRID 1271552 reaction equation
[C:1]([C:3]1[C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[ClH:16]>C(O)C.[Pd]>[ClH:16].[ClH:16].[NH2:2][CH2:1][C:3]1[C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 220385682-Cyano-3-(ethoxycarbonylmethoxy)pyridine

Product 1

HCID 220385702-Aminomethyl-3-(ethoxycarbonylmethoxy)pyridine dihydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-cyano-3-(ethoxycarbonylmethoxy)pyridine (3.2 g, 15.52 mmol) in 180 ml of ethanol is added concentrated aqueous HCl (2.92 ml, 35 mmol) and 10% palladium on charcoal (1.5 g). After stirring for 4 hours under a hydrogen pressure of 4 bar, the mixture is filtered through celite, rinsed with ethanol and evaporated. The 2-aminomethyl-3-(ethoxycarbonylmethoxy)pyridine dihydrochloride thus obtained is sufficiently pure and used in the next step without further purification. Yield: 3.82 g (100%).

Workup

  1. filtrationthe mixture is filtered through celite
  2. washrinsed with ethanol
  3. customevaporated

Sources & evidence

ORD record
ord-5838cc3e88a14c5584a765380e7239d8
Source dataset
uspto-grants-2007_04
Patent number
US07205407B2

Reaction notes

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