Hydrochloric Acid → 3-(Aminomethyl)-4-ethyl-6-methylpyridin-2(1H)-one hydrochloride

HRID 2206612Notes

Reaction equation

HRID 2206612 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[C:10](=[O:18])[NH:11][C:12]([CH3:17])=[CH:13][C:14]=1[CH2:15][CH3:16])(C)(C)C.[ClH:20]>O1CCOCC1>[ClH:20].[NH2:7][CH2:8][C:9]1[C:10](=[O:18])[NH:11][C:12]([CH3:17])=[CH:13][C:14]=1[CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 117804509HCID 117804509, compound

Product 1

HCID 674665823-(Aminomethyl)-4-ethyl-6-methylpyridin-2(1H)-one hydrochlorideYield 77.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl((4-ethyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamate (1.00 g, 3.75 mmol) was dissolved in a solution of hydrogen chloride in 1,4-dioxane (20 mL). The mixture was stirred for 2 hr. The reaction mixture was filtered. The residue was washed with dichloromethane, dried to afford 3-(aminomethyl)-4-ethyl-6-methylpyridin-2(1H)-one hydrochloride (593 mg, 77.9%) as a light yellow solid. LRMS (M+H+) m/z: calcd 166.11. found 167.1. 1H NMR (400 MHz, D2O): δ ppm 6.31 (s, 1H), 4.06 (s, 2H), 2.57 (q, J=7.86 Hz, 2H), 2.25 (s, 3H), 1.10 (t, J=7.53 Hz, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washThe residue was washed with dichloromethane
  3. customdried

Sources & evidence

ORD record
ord-09be5b705b07479fbaec3b17971189b6
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

Loading…