Ammonia → 6-Methylnicotinamide

HRID 2197209Notes

Reaction equation

HRID 2197209 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][N:3]=1.[NH3:12]>>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH2:12])=[O:7])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 231548Methyl 6-methylnicotinate

Product 1

HCID 963516-MethylnicotinamideYield 72%

Procedure

A mixture of methyl 6-methylnicotinate (13.9 g) and 28% aqueous ammonia (140 mL) was stirred at room temperature for 4 hr. The reaction mixture was concentrated under reduced pressure, and the residue was recrystallized from ethanol to give the title compound as a white solid (yield 8.98 g, 72%). 1H-NMR (CDCl3) δ: 2.63 (3H, s), 5.60-6.20 (2H, brm), 7.25-7.28 (1H, m), 8.04-8.07 (1H, m), 8.90 (1H, d, J=2.1 Hz).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-33ca16c507d24c7286e21652b92c67e7
Source dataset
uspto-grants-2012_12
Patent number
US08338462B2

Reaction notes

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