Ammonia → 6-Isobutyl-5-methylnicotinamide

HRID 2065893Notes

Reaction equation

HRID 2065893 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([CH2:12][CH:13]([CH3:15])[CH3:14])=[N:7][CH:6]=1)C.[NH3:17]>CO>[CH2:12]([C:8]1[C:9]([CH3:11])=[CH:10][C:5]([C:4]([NH2:17])=[O:3])=[CH:6][N:7]=1)[CH:13]([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 574372006-Isobutyl-5-methylnicotinic acid ethyl ester

Product 1

HCID 670268976-Isobutyl-5-methylnicotinamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-isobutyl-5-methyl-nicotinic acid ethyl ester (2.86 g, 12.9 mmol) in 7 N NH3 in MeOH (80 mL) is stirred at 60° C. for 20 h before the solvent is removed in vacuo. The residue is dried to give 6-isobutyl-5-methyl-nicotinamide (1.89 g) as a yellow oil; LC-MS: tR=0.66 min, [M+1]+=193.29; 1H NMR (D6-DMSO): δ 0.91 (d, J=6.5 Hz, 6H), 2.08-2.20 (m, 1H), 2.32 (s, 3H), 2.65 (d, J=7.3 Hz, 2H), 7.43 (s, 1H), 7.95 (s, 1H), 8.01 (m, 1H), 8.78 (s, 1H).

Workup

  1. customis removed in vacuo
  2. customThe residue is dried

Sources & evidence

ORD record
ord-faea7357c6fb4b849d2984c446673800
Source dataset
uspto-grants-2012_10
Patent number
US08288554B2

Reaction notes

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