HCID 86723688, compound → 3-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one

HRID 577452Notes

Reaction equation

HRID 577452 reaction equation
C[O:2][C:3]1[C:8]([CH2:9][NH:10]C(=O)OC(C)(C)C)=[C:7]([CH3:18])[CH:6]=[C:5]([CH3:19])[N:4]=1>Cl>[NH2:10][CH2:9][C:8]1[C:3](=[O:2])[NH:4][C:5]([CH3:19])=[CH:6][C:7]=1[CH3:18]

Participants

3

Reactant 1

HCID 86723688HCID 86723688, compound

Product 1

HCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneYield 97.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of tert-butyl [(2-methoxy-4,6-dimethylpyridin-3-yl)methyl]carbamate (Cpd U, 140 g, 0.52 mol) in 6N HCl (500 mL) was heated at 100° C. and stirred for six hours. The reaction mixture was concentrated and the residue was re-crystallized with EtOH to afford the title compound (Cpd V, 77 g, 55%) as hydrochloride salts. 1H NMR (400 MHz, D2O) δ 6.31 (s, 1H), 4.11 (s, 2H), 2.31-2.30 (s, 6H); MS 175.1 [M+Na].

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was re-crystallized with EtOH

Sources & evidence

ORD record
ord-b0e294ded0f842ab826943c6e8f29478
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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