Ammonium Hydroxide → 2-Chloro-4-methylpyridine-3-carboxamide

HRID 1873066Notes

Reaction equation

HRID 1873066 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[CH:5]=[CH:4][N:3]=1.[OH-:11].[NH4+]>OS(O)(=O)=O>[Cl:1][C:2]1[C:7]([C:8]([NH2:9])=[O:11])=[C:6]([CH3:10])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 123877362-Chloro-4-methyl-nicotinonitrile

Product 1

HCID 109428862-Chloro-4-methylpyridine-3-carboxamideYield 69%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 6.33 g of 2-chloro-4-methyl-3-pyridine carbonitrile (9) in 6 mL concentrated H2SO4 was stirred at 100° C. for one hour, added ice water, made alkaline with ammonium hydroxide and extracted with ethyl acetate. The extract was dried and the solvent removed to leave a crystalline residue. Recrystallization from ethyl acetate gave 4.9 g (69%) of (10).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extract was dried
  3. customthe solvent removed
  4. customto leave a crystalline residue
  5. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-6ff931a77aef49049696122b83f1db21
Source dataset
uspto-grants-2000_08
Patent number
US06111112

Reaction notes

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