Formamide → 6-Methoxy-7-nitroquinazolin-4(3H)-one

HRID 634741Notes

Reaction equation

HRID 634741 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([O:14][CH3:15])=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH:16]([NH2:18])=O>O>[CH3:15][O:14][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][C:9]=1[N+:11]([O-:13])=[O:12])[N:1]=[CH:16][NH:18][C:4]2=[O:6]

Participants

4

Reactant 2

HCID 713FormamideHCID 212602732-Amino-4-nitro-5-methoxybenzoic Acid

Product 1

HCID 1354520046-Methoxy-7-nitroquinazolin-4(3H)-oneYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-amino-5-methoxy-4-nitrobenzoic acid (1 6.6 g, 78 mmol) in formamide (250 ml) was heated at reflux for 4.5 hours. The reaction mixture was cooled to 0° C., diluted with water and the resulting precipitate collected by filtration, washed with water and dried under vacuum to give 6-methoxy-7-nitro-3,4-dihydroquinazolin-4-one ( 11.56 g, 67%).

Workup

  1. temperatureat reflux for 4.5 hours
  2. filtrationthe resulting precipitate collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-ed43d6a74e77410e8317dfed80d62c92
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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