Ammonia → 2-AMINO-6-METHYLNICOTINIC ACID

HRID 1192405Notes

Reaction equation

HRID 1192405 reaction equation
Cl[C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH3:12]>CO>[NH2:12][C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 1217242-Chloro-6-methylnicotinic acid

Product 1

HCID 27344322-AMINO-6-METHYLNICOTINIC ACIDYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-Chloro-6-methyl-nicotinic acid (3.00 g, 17.5 mmol) in ammonia in MeOH (7M, 60 mL) in a bomb was heated to 120° C. overnight. After cooling, the solvent was removed and the residue was neutralized with 2N HCl. The precipitate was filtered, washed with water and dried to afford 2-Amino-6-methyl-nicotinic acid (1.44 g, 54%). 1H NMR (CD3OD, 400 MHz) δ 8.21 (d, J=7.6 Hz, 1H), 6.60 (d, J=7.6 Hz, 1H), 2.41 (s, 3H). MS (APCI+) [M+H]+153.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-75197663f05245b1952fedd4fbd056f7
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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