Acetic Anhydride → 5-(4-Acetamidophenyl)-3-methyl-2(1H)-pyrazinone

HRID 542451Notes

Reaction equation

HRID 542451 reaction equation
Br.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH3:16])[C:12](=[O:15])[NH:13][CH:14]=2)=[CH:5][CH:4]=1.[C:17](OC(=O)C)(=[O:19])[CH3:18].C([O-])(=O)C.[Na+]>O>[C:17]([NH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[C:11]([CH3:16])[C:12](=[O:15])[NH:13][CH:14]=2)=[CH:7][CH:8]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 202086515-(4-Aminophenyl)-3-methyl-2(1H)-pyrazinone hydrobromide

Product 1

HCID 138535655-(4-Acetamidophenyl)-3-methyl-2(1H)-pyrazinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(4-Aminophenyl)-3-methyl-2(1H)-pyrazinone hydrobromide (1.0 g) in water (25 ml) was treated with acetic anhydride and sodium acetate in a similar manner to that described in Example 3. On recrystallisation from aqueous acetic acid the title compound (0.68 g) had m.p. >300° C.; δ(DMSO-d6) inter alia 2.08 (3H, s, CO--CH3), 2.39 (3H, d, 3---CH3), 10.0 (1H, s, NHCO); ν(Nujol mull) 1655 (C=O) cm-1.

Workup

  1. customOn recrystallisation from aqueous acetic acid the title compound (0.68 g)

Sources & evidence

ORD record
ord-595dc71e12104417ab19e7752504a160
Source dataset
uspto-grants-1987_04
Patent number
US04657906

Reaction notes

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