Ammonia → 2-Ethyl-6-methyl-isonicotinamide

HRID 1908826Notes

Reaction equation

HRID 1908826 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([CH2:12][CH3:13])[CH:6]=1)C.[NH3:15]>CO>[CH2:12]([C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([CH3:11])[N:8]=1)[C:4]([NH2:15])=[O:3])[CH3:13]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 669333672-Ethyl-6-methylisonicotinic acid ethyl ester

Product 1

HCID 670269782-Ethyl-6-methyl-isonicotinamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-ethyl-6-methyl-isonicotinic acid ethyl ester (3.90 g, 20.2 mmol, prepared in analogy to the corresponding tert.-butyl ester) in 7 N NH3 in methanol (50 mL) is stirred in a sealed vessel at 60° C. for 20 h. The solvent is evaporated and the residue is suspended in diethyl ether. The solid material is collected, washed with additional diethyl ether and dried under HV to give 2-ethyl-6-methyl-isonicotinamide (2.85 g) as a white powder; LC-MS: tR=0.26 min, [M+1]+=165.05; 1H NMR (D6-DMSO): δ 1.23 (t, J=7.5 Hz, 3H), 2.49 (s, 3H), 2.75 (q, J=7.8 Hz, 2H), 7.44 (s, 2H), 7.59 (s br, 1H), 8.11 (s br, 1H).

Workup

  1. customThe solvent is evaporated
  2. customThe solid material is collected
  3. washwashed with additional diethyl ether
  4. customdried under HV

Sources & evidence

ORD record
ord-9ede796f9d184f569cea92c11774df9f
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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