Hydrochloric Acid → 3-AMinoMethyl-6-Methyl-4-propyl-1H-pyridin-2-one hydrochloride

HRID 2208653Notes

Reaction equation

HRID 2208653 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]#[N:10])=[C:4]([CH2:11][CH2:12][CH3:13])[CH:3]=1.[ClH:14]>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[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 156418016-Methyl-2-oxo-4-propyl-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 708741233-AMinoMethyl-6-Methyl-4-propyl-1H-pyridin-2-one hydrochlorideYield 60%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 6-methyl-2-oxo-4-propyl-1,2-dihydropyridine-3-carbonitrile (15.0 g, 85.1 mmol) in methanol (600 mL) and concentrated HCl (15 mL) was added Pd(OH)2 (15.0 g). The mixture was stirred for 48 hours under H2 atmosphere. The reaction mixture was filtered and filtrate was concentrated in vacuo. Ethanol was added to the residue, the resulting precipitate was collected and dried to give the titled compound as a white solid (13.0 g, 60% yield). 1H-NMR (400 MHz, CDCl3) δppm; 11.86 (br. s., 1H), 6.00 (s, 1H), 3.78 (q, J=5.5 Hz, 2H), 3.61 (br. s., 2H), 2.46 (m, 2H), 2.17 (s, 3H), 1.50 (sxt, J=7.4 Hz, 2H), 0.91 (t, J=7.4 Hz, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationfiltrate was concentrated in vacuo
  3. additionEthanol was added to the residue
  4. customthe resulting precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-564a4425e24e45e5ad85d2751ae845a4
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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