Hydrochloric Acid → 6-Amino-4-methylnicotinic acid

HRID 1740949Notes

Reaction equation

HRID 1740949 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])C(C#N)=[CH:4][N:3]=1.[OH-:11].[Na+].Cl.[CH2:14]([OH:16])[CH3:15]>O>[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:15]([C:14]([OH:11])=[O:16])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 14798Sodium HydroxideHCID 99641036-Amino-4-methylnicotinonitrile

Product 1

HCID 99641496-Amino-4-methylnicotinic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-amino-5-cyano-4-methylpyridine (600 mg, 4.50 mmol) in ethanol (7.5 mL) was treated with 10N sodium hydroxide (7.5 mL) for 24 h at reflux temperature. The mixture was cooled and diluted with water (30 mL). The pH was adjusted to 7 with conc. hydrochloric acid and 1N hydrochloric acid. The resulting solid was filtered, dried by suction, washed with ether, and dried in vacuo; yield 134 mg (20%).

Workup

  1. temperatureat reflux temperature
  2. temperatureThe mixture was cooled
  3. filtrationThe resulting solid was filtered
  4. customdried by suction
  5. washwashed with ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-ef5ac309499b4f3e8dbf6cd0ea6d7ef5
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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