Hydrochloric Acid → 3-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one hydrochloride

HRID 1469151Notes

Reaction equation

HRID 1469151 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[C:10]#[N:11].N#N.[ClH:14]>CO.[OH-].[OH-].[Pd+2]>[ClH:14].[NH2:11][CH2:10][C:3]1[C:4](=[O:9])[NH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 947Nitrogen2×HCID 698563-Cyano-4,6-dimethyl-2-hydroxypyridine

Product 1

HCID 438104513-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one hydrochlorideYield 90%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (10.0 g, 67.5 mmol) in MeOH (1.50 L) and conc. HCl (30 mL) was added 10% Pd(OH)2 (19 g) under N2 atmosphere. The N2 gas was displaced by H2 gas and the mixture was stirred for 26 hours at RT under hydrogen atmosphere. The H2 gas was displaced by N2 gas. The mixture was filtered through Celite, washed with MeOH and concentrated. The residue was triturated with EtOH, collected with Buchner funnel, and dried under vacuum pressure to give the titled compound as a white solid (11.5 g, 90%). 1H NMR (400 MHz, DMSO-d6): δ ppm 11.86 (brs, 1H), 5.98 (s, 1H), 3.78 (m, 2H), 2.20 (s, 3H), 2.16 (s, 3H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with MeOH
  3. concentrationconcentrated
  4. customThe residue was triturated with EtOH
  5. customcollected with Buchner funnel
  6. customdried under vacuum pressure

Sources & evidence

ORD record
ord-d50aa90e7fe24ed1b15a1ae8d4281297
Source dataset
uspto-grants-2015_04
Patent number
US09006242B2

Reaction notes

Loading…