Acetic Anhydride → HCID 13060166, compound

HRID 2286658Notes

Reaction equation

HRID 2286658 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[NH2:8][C:9]1[N:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:11][CH:10]=1>C(O)=O>[CH:1]([NH:8][C:9]1[N:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:11][CH:10]=1)=[O:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13809143Methyl 6-aminopyridine-2-carboxylate

Product 1

HCID 13060166HCID 13060166, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of formic acid (559.3 g.) and acetic anhydride (1033.4 g.) was stirred for 30 minutes at 40° to 50° C. and thereto was added methyl 6-amino-2-pyridinecarboxylate (616 g.) at 40° C., and then the mixture was stirred for 1 hour at 80° C. After the removal of the solvent from the reaction mixture, the residue was dissolved in a mixture of benzene and n-hexane and then filtered. Thus obtained precipitates were recrystallized from benzene (2 l.) to give methyl 6-formamido-2-pyridinecarboxylate (647.8 g.), mp 134° to 136° C.

Workup

  1. stirringthe mixture was stirred for 1 hour at 80° C
  2. customAfter the removal of the solvent from the reaction mixture
  3. dissolutionthe residue was dissolved in a mixture of benzene and n-hexane
  4. filtrationfiltered
  5. customThus obtained
  6. customprecipitates
  7. customwere recrystallized from benzene (2 l.)

Sources & evidence

ORD record
ord-a4ba57eff2894013a46e119e675e425e
Source dataset
uspto-grants-1981_05
Patent number
US04267176

Reaction notes

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