Hydrochloric Acid → 2-Amino-5-aminomethyl-6-methylpyridine dihydrochloride

HRID 361373Notes

Reaction equation

HRID 361373 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[C:4]([CH3:10])[N:3]=1.[ClH:11]>C(O)C.CO.O.[Pd]>[ClH:11].[ClH:11].[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[C:4]([CH3:10])[N:3]=1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 27946626-Amino-2-methylpyridine-3-carbonitrile

Product 1

HCID 665242322-Amino-5-aminomethyl-6-methylpyridine dihydrochlorideYield 94%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-amino-5-cyano-6-methylpyridine (4.0 g, 30.0 mmol) and 10% Pd/C (3.08 g) in ethanol (80 mL), methanol (30 mL), concentrated HCl (6 mL) and water (10 mL) was shaken on a Parr apparatus at 60 psi for 25 h. The reaction was filtered through celite, rinsing with 1:1 ethanol/methanol and was evaporated in vacuo to a solid, which was triturated with 5:1 ethyl acetate/ethanol to give the title compound (5.95 g, 94%):

Workup

  1. filtrationThe reaction was filtered through celite
  2. washrinsing with 1:1 ethanol/methanol
  3. customwas evaporated in vacuo to a solid, which
  4. customwas triturated with 5:1 ethyl acetate/ethanol

Sources & evidence

ORD record
ord-005ebb459f8a4b5a8eaf04de830958ff
Source dataset
uspto-grants-1999_02
Patent number
US05866573

Reaction notes

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