Ammonium Hydroxide → 4-Chloropyridine-2-carboxamide

HRID 2361649Notes

Reaction equation

HRID 2361649 reaction equation
[OH-].[NH4+:2].[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([O:12]C)=O)[CH:5]=1>CO>[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([NH2:2])=[O:12])[CH:5]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 820890Methyl 4-Chloropicolinate

Product 1

HCID 3035434-Chloropyridine-2-carboxamideYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Ammonium hydroxide (2 ml) was added to methyl 4-chloropyridine-2-carboxylate (100 mg, 0.58 mmol) in MeOH (4 ml) in a sealed tube and heated at 50° C. for 4 hours. The reaction was cooled to room temperature and concentrated at reduced pressure. The residue was dissolved in dichloromethane (20 ml), washed with water (2×10 ml), dried (Na2SO4), filtered and concentrated at reduced pressure to give the title compound (66 mg, 72%).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated at reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane (20 ml)
  4. washwashed with water (2×10 ml)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-43f6416a74724a95a06dc7a4b02b0ec7
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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