Nitric Acid → 6-Nitro-4-oxo-3,4-dihydroquinazoline-8-carboxylic acid

HRID 578640Notes

Reaction equation

[O:1]=[C:2]1[C:11]2[C:6](=[C:7]([C:12]([OH:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][NH:3]1.[N+:15]([O-])([OH:17])=[O:16]>S(=O)(=O)(O)O>[N+:15]([C:9]1[CH:10]=[C:11]2[C:6](=[C:7]([C:12]([OH:14])=[O:13])[CH:8]=1)[N:5]=[CH:4][NH:3][C:2]2=[O:1])([O-:17])=[O:16]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 4-oxo-3,4-dihydroquinazoline-8-carboxylic acid (500 mg, 2.63 mmol) in 3 mL of sulfuric acid at 0° C., fuming nitric acid was added portionly. The resulting mixture was then stirred at 60° C. overnight. After cooling to rt, the reaction mixture was poured into ice-water slowly. The yellow precipitate was collected by filtration, and washing with water as the desired product in 84% yield. 1HNMR (in DMSO): 8.60 (s, 1H), 8.89 (d, J=2.6 Hz, 1H), 8.91 (d, J=2.6 Hz, 1H). Mass: M+H+: 236.

Workup

additionwas added portionly
temperatureAfter cooling to rt
filtrationThe yellow precipitate was collected by filtration
washwashing with water as the desired product in 84% yield

Sources & evidence

ORD record: ord-a056dc5bf1cd4613b5ac433d2926c858
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040560B2

Reaction notes

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