Acetic Anhydride → Methyl 4-(acetylamino)pyridine-3-carboxylate

HRID 539941

Reaction equation

HRID 539941 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]([O:10][CH3:11])=[O:9].[C:12](OC(=O)C)(=[O:14])[CH3:13]>O1CCOCC1>[C:12]([NH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]([O:10][CH3:11])=[O:9])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 592353Methyl 4-aminopyridine-3-carboxylate

Product 1

HCID 66524315Methyl 4-(acetylamino)pyridine-3-carboxylateYield 42.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 4-aminopyridine-3-carboxylate (100 g, 0.6 mol) and acetic anhydride (240 g, 2.4 mol) in anhydrous 1,4-dioxane (1.2 L) was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and diluted with water (800 mL). The mixture was neutralized with a saturated aqueous solution of sodium bicarbonate to pH 7. The formed solid was collected by filtration and dried in vacuo to afford 50 g of methyl 4-(acetylamino)pyridine-3-carboxylate as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with water (800 mL)
  3. filtrationThe formed solid was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-da271d1338104b47a3d098c5128eb4f3
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Linked notes

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