Hydrochloric Acid → 3-(Aminomethyl)-6-methyl-4-(2-propyl)-1,2-dihydropyridin-2-one HCl salt

HRID 2208655Notes

Reaction equation

HRID 2208655 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]#[N:10])=[C:4]([CH:11]([CH3:13])[CH3:12])[CH:3]=1.[ClH:14].N#N>CO.[OH-].[OH-].[Pd+2]>[ClH:14].[NH2:10][CH2:9][C:5]1[C:6](=[O:8])[NH:7][C:2]([CH3:1])=[CH:3][C:4]=1[CH:11]([CH3:12])[CH3:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 947Nitrogen2×HCID 103973143-cyano-4-isopropyl-6-methyl-2(1H)-pyridinone

Product 1

HCID 867195293-(Aminomethyl)-6-methyl-4-(2-propyl)-1,2-dihydropyridin-2-one HCl saltYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 6-methyl-2-oxo-4-(propan-2-yl)-1,2-dihydropyridine-3-carbonitrile (5.00 g, 28.4 mmol) and in MeOH (400 ml) and HCl (8.8 ml, 12 M) was added 10% Pd(OH)2 (5.17 g, 3.68 mmol) under N2 atmosphere. The N2 gas was displaced by H2 gas and the mixture was stirred for 24 h at 23° C. under hydrogen. The H2 gas was displaced by N2 gas and the mixture was filtered through celite, washed with MeOH and concentrated. The residue was triturated with EtOH-TBME, the solid was collected with Buchner funnel and dried in vacuo to give the titled compound (6.15 g, 100%). 1H NMR (400 MHz, DMSO-d6): δ ppm 11.9 (br-s, 1H), 8.03 (br-s, 2H), 6.12 (s, 1H), 3.82-3.84 (m, 2H), 3.08-3.12 (m, 1H), 2.19 (s, 3H), 1.12 (d, J=6.8 Hz, 6H).

Workup

  1. filtrationthe mixture was filtered through celite
  2. washwashed with MeOH
  3. concentrationconcentrated
  4. customThe residue was triturated with EtOH-TBME
  5. customthe solid was collected with Buchner funnel
  6. customdried in vacuo

Sources & evidence

ORD record
ord-92be28c99b68460286023fde82c77540
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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