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

HRID 1696559Notes

Reaction equation

HRID 1696559 reaction equation
[CH:1]([NH2:3])=O.[NH2:4][C:5]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:6]=1[C:7]([OH:9])=O>O>[N+:14]([C:11]1[CH:10]=[C:6]2[C:5](=[CH:13][CH:12]=1)[N:4]=[CH:1][NH:3][C:7]2=[O:9])([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 713FormamideHCID 120322-Amino-5-nitrobenzoic acid

Product 1

HCID 1353985026-Nitro-3,4-dihydroquinazolin-4-oneYield 61.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
155 °C

Procedure

A mixture of formamide (14 g, 0.3 mol) and 2-amino-5-nitrobenzoic acid (9.1 g, 0.05 mol) was heated at 155° C. for 7 h, cooled to RT and stirred overnight. The mixture was diluted with H2O (30 mL) and filtered. The resultant brown solid was dissolved in i-PrOH (300 mL), warmed to reflux, cooled to RT and filtered and dried to yield 6-nitroquinazolin-4(3H)-one, (5.85 g, 61% yield). MS (ESI) m/e (M+H+) 192.0

Workup

  1. temperaturecooled to RT
  2. filtrationfiltered
  3. dissolutionThe resultant brown solid was dissolved in i-PrOH (300 mL)
  4. temperaturewarmed
  5. temperatureto reflux
  6. temperaturecooled to RT
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-1cfbed8f5c7949e1aca7031ae1877b2e
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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