Acetic Anhydride → HCID 15171503, compound

HRID 259767Notes

Reaction equation

HRID 259767 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-2-aminopyridine. 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-e23a6f8f1284447e97ebbb2106cdfd4c
Source dataset
uspto-grants-1996_06
Patent number
US05523318

Reaction notes

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