Ammonia → HCID 67027001, compound

HRID 1908834Notes

Reaction equation

HRID 1908834 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]([CH2:11][OH:12])[CH:5]=1.[NH3:14]>CO>[OH:12][CH2:11][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([CH3:10])[N:7]=1)[C:3]([NH2:14])=[O:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 67026976HCID 67026976, compound

Product 1

HCID 67027001HCID 67027001, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-hydroxymethyl-6-methyl-isonicotinic acid methyl ester (400 mg, 2.21 mmol) in 7 N NH3 in methanol (25 mL) is stirred in a sealed vessel at 70° C. for 24 h. The mixture is cooled to rt, the solvent is removed in vacuo and the residue is dried under HV to give crude 2-hydroxymethyl-6-methyl-isonicotinamide (400 mg) as a pale yellow solid; LC-MS: tR=0.21 min, [M+1]+=167.01; 1H NMR (D6-DMSO): δ 2.50 (s, 3H), 4.56 (d, J=5.5 Hz, 2H), 5.44 (t, J=5.8 Hz, 1H), 7.49 (s, 1H), 7.58 (s br, 1H), 7.67 (s, 1H), 8.16 (s br, 1H).

Workup

  1. customthe solvent is removed in vacuo
  2. customthe residue is dried under HV

Sources & evidence

ORD record
ord-033e78b041314fa88e5823e57b6e60c5
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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