Acetic Anhydride → HCID 15171503, compound

HRID 234886Notes

Reaction equation

HRID 234886 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10]>C(Cl)Cl>[C:9]([NH:8][C:7]1[C:2]([NH2:1])=[N:3][CH:4]=[CH:5][CH:6]=1)(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 99562,3-Diaminopyridine

Product 1

HCID 15171503HCID 15171503, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3-Diaminopyridine (28 g, 0.256 mole) and acetic anhydride (30 mL, 0.38 mole) were stirred at room temp in methylene chloride (770 mL) for 30 min. The mixture was concentrated in vacuo to a brown solid. Recrystallization from methylene chloride/hexane (10/1) gave off-white crystals (21.9 g, 57%) of 3-acetamido-2aminopyridine. This acetamide was combined with 3-chloro-2,4-pentanedione (20 g, 0.146 mole) in abs. ethanol (350 mL) and stirred under reflux for 20 hrs. After cooling, the mixture was diluted with methylene chloride (300 mL) and washed with water (3×300 mL). The organic phase was dried over magnesium sulfate and concentrated to a green solid. Recrystallization from methylene chloride/hexane (1/1) gave the title compound as green crystals (7.3 g, 21%, m.p. 173°-175° C.).

Workup

  1. concentrationThe mixture was concentrated in vacuo to a brown solid
  2. customRecrystallization from methylene chloride/hexane (10/1)

Sources & evidence

ORD record
ord-39282c457468492ca6633e378fd89e0d
Source dataset
uspto-grants-1997_01
Patent number
US05597816

Reaction notes

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