Acetic Anhydride → 5-(4-acetamidophenyl)-2(1H)-pyrazinone

HRID 542449Notes

Reaction equation

HRID 542449 reaction equation
Br.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[CH:11][C:12](=[O:15])[NH:13][CH:14]=2)=[CH:5][CH:4]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17].C([O-])(=O)C.[Na+]>O>[C:16]([NH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[CH:11][C:12](=[O:15])[NH:13][CH:14]=2)=[CH:7][CH:8]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 202086625-(4-Aminophenyl)-2(1H)-pyrazinone hydrobromide

Product 1

HCID 69179095-(4-acetamidophenyl)-2(1H)-pyrazinoneYield 39.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(4-Aminophenyl)-2(1H)-pyrazinone hydrobromide (2.5 g) in water (20 ml) was treated with acetic anhydride (1.2 g) and anhydrous sodium acetate (1.4 g). The mixture was stirred at room temperature for 1 hour, and the crude product (1.58 g; m.p. 268°-275° C.) was filtered off. This material was thoroughly washed with water and recrystallised from glacial acetic acid to give 5-(4-acetamidophenyl)-2(1H)-pyrazinone (0.84 g; m.p. 287°-8° C.).

Workup

  1. filtrationthe crude product (1.58 g; m.p. 268°-275° C.) was filtered off
  2. washThis material was thoroughly washed with water
  3. customrecrystallised from glacial acetic acid

Sources & evidence

ORD record
ord-70d06a5fcb4d44399adbd6a50cdca3bb
Source dataset
uspto-grants-1987_04
Patent number
US04657906

Reaction notes

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