Hydrochloric Acid → (2-Methoxypyridin-4-yl)methanamine

HRID 557331

Reaction equation

HRID 557331 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([O:9][CH3:10])[CH:4]=1)#[N:2].Cl.CCOCC>CO.[Pd]>[CH3:10][O:9][C:5]1[CH:4]=[C:3]([CH2:1][NH2:2])[CH:8]=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 72048872-Methoxyisonicotinonitrile

Product 1

HCID 16227983(2-Methoxypyridin-4-yl)methanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

4-Cyano-2-methoxypyridine (1.7 g) was dissolved in MeOH (50 ml) and conc. HCl (4.96 ml) was added. Pd/C (10%) was added and H2 was added and let stand overnight. The solids were filtered through Celite® and the cake was washed with MeOH (˜250 ml). Concentration in vacuo produced an oil which was dissolved in MeOH (˜20 ml). Et2O (200 ml) was added and stirred for 1 h. The resulting precipitate was filtered and washed with Et2O to afford (2-methoxypyridin-4-yl)methylamine (hydrochloride salt) as an off-white solid.

Workup

  1. additionH2 was added
  2. filtrationThe solids were filtered through Celite®
  3. washthe cake was washed with MeOH (˜250 ml)
  4. concentrationConcentration in vacuo
  5. customproduced an oil which
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with Et2O

Sources & evidence

ORD record
ord-5a454aba9fe44d4d88363e3cb7e9de93
Source dataset
uspto-grants-2011_11
Patent number
US08058445B2

Linked notes

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