Sodium Acetate → 3-(Aminomethyl)-4-methyl-6-propyl-2(1H)-pyridinone

HRID 62363Notes

Reaction equation

HRID 62363 reaction equation
C([O-])(=O)C.[Na+].[CH3:6][C:7]1[CH:12]=[C:11]([CH2:13][CH2:14][CH3:15])[NH:10][C:9](=[O:16])[C:8]=1[C:17]#[N:18]>[Pd].C(O)(=O)C.[Pt]=O>[NH2:18][CH2:17][C:8]1[C:9](=[O:16])[NH:10][C:11]([CH2:13][CH2:14][CH3:15])=[CH:12][C:7]=1[CH3:6]

Participants

6

Reactant 2

HCID 517045Sodium AcetateHCID 138379154-Methyl-2-oxo-6-propyl-1,2-dihydro-3-pyridinecarbonitrile

Product 1

HCID 671243293-(Aminomethyl)-4-methyl-6-propyl-2(1H)-pyridinone

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent2×

Procedure

Sodium acetate (3.5 g, 42.6 mmol), palladium on carbon (0.81 g) and platinum oxide (0.1 g) were placed in a dried Parr bottle flushed with nitrogen, followed by addition of a small amount of acetic acid (to wet the catalysts). A solution of 4-methyl-2-oxo-6-propyl-1,2-dihydro-pyridine-3-carbonitrile (5 g, 28 mmol) in acetic acid was added to the Parr bottle followed by additional acetic acid (200 mL). The vessel was capped, placed on Parr apparatus and hydrogenated at 45 psi for 12 h. The reaction mixture was filtered and the filtrate concentrated in vacuo. The crude product was purified by preparative HPLC to afford the title compound (TFA salt) as 4.1 g (87%). LCMS E-S (M+H))=181.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.8-11.9 (br s, 1H), 7.83-7.88 (br s, 3H), 5.99 (s, 1H), 3.77-3.81 (m, 2H), 2.37 (t, 2H), 1.53 (m, 2H), 0.83 (t, 3H).

Workup

  1. customflushed with nitrogen
  2. additionfollowed by addition of a small amount of acetic acid (
  3. customThe vessel was capped
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-0ba99f83419c4e3cb93dd6043a2b52d5
Source dataset
uspto-grants-2016_09
Patent number
US09446041B2

Reaction notes

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