Acetyl chloride → Methyl 6-aminopyridine-2-carboxylate

HRID 2233887Notes

Reaction equation

HRID 2233887 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.[C:11](Cl)(=O)C>CO>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 3516526-Aminopyridine-2-carboxylic acid

Product 1

HCID 13809143Methyl 6-aminopyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

6-Aminopyridine-2-carboxylic acid (5.0 g, 36 mmol) was dissolved in 50 ml of MeOH. To this was added acetyl chloride (9.0 ml, 126 mmol) in 50 ml of MeOH. The reaction was heated to reflux overnight. Concentrate to an orange oil and partition with EtOAc and water. The organic portions were washed with brine, dried (MgSO4) and concentrated to a yellow solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. concentrationConcentrate to an orange oil
  4. custompartition with EtOAc and water
  5. washThe organic portions were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated to a yellow solid

Sources & evidence

ORD record
ord-5f994ab462f64d76b40e7b63c3bb203c
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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