Acetic Acid → 7-acetamido-6-nitro-3H-quinazolin-4-one

HRID 1489586Notes

Reaction equation

HRID 1489586 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[C:16](O)(=[O:18])[CH3:17].C(OC(=O)C)(=O)C>O>[C:16]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 1356184907-amino-6-nitro-3H-quinazolin-4-one

Product 1

HCID 1356184917-acetamido-6-nitro-3H-quinazolin-4-oneYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 7-amino-6-nitro-3H-quinazolin-4-one (5.90 g, 28.6 mmol) [Leonard, N. J.; Morrice, A. G.; Sprecker, M. A.; J. Org. Chem., 1975, 40, 356-363] in a mixture of glacial acetic acid (300 mL) and acetic anhydride (100 mL) is heated under reflux for 6 h, and water (100 mL) is added. The solution is then concentrated to a small volume to give 7-acetamido-6-nitro-3H-quinazolin-4-one (5.37 g, 76%). 1H NMR (DMSO) δ10.51 (1H, brs), 8.57 (1H, s), 8.24 (1H, s), 7.97 (1H, s), 2.15 (3H, s).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 6 h
  3. concentrationThe solution is then concentrated to a small volume

Sources & evidence

ORD record
ord-2dcd7ce2f4fe474ea053c76070ada30d
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

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