Formamide → 6-Nitro-3,4-dihydroquinazolin-4-one

Reaction equation

[N+:1]([C:4]1[CH:12]=[C:8]([C:9]([OH:11])=O)[C:7]([NH2:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:14]([NH2:16])=O>>[N+:1]([C:4]1[CH:12]=[C:8]2[C:7](=[CH:6][CH:5]=1)[N:13]=[CH:14][NH:16][C:9]2=[O:11])([O-:3])=[O:2]

Participants

Reactant 2

HCID 713Formamide

HCID 120322-Amino-5-nitrobenzoic acid

Product 1

HCID 1353985026-Nitro-3,4-dihydroquinazolin-4-oneYield 82%

Procedure

Using an analogous procedure to that described in the first paragraph of the portion of Example 1 which is concerned with the preparation of starting materials, 5-nitroanthranilic acid was reacted with formamide to give 6-nitroquinazolin-4-one in 82% yield, m.p. 268°-271° C.

Sources & evidence

ORD record: ord-66692aa56892493bab2bcf912181f8a8
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05616582

Reaction notes

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