Formamide → 7-Nitroquinazolin-4(3H)-one

HRID 468552Notes

Reaction equation

HRID 468552 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:13])[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=O)([O-:3])=[O:2].[CH:14]([NH2:16])=O>>[N+:1]([C:4]1[CH:5]=[C:6]2[C:7]([C:8](=[O:10])[NH:16][CH:14]=[N:13]2)=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 713FormamideHCID 120764-Nitroanthranilic acid

Product 1

HCID 862228007-Nitroquinazolin-4(3H)-oneYield 95%

Conditions

Temperature
165 °C

Procedure

A mixture of 4-nitroanthranilic acid (2.17 g, 11.91 mmol) and formamide (1.5 mL, 38.43 mmol) was heated at 165° C. for 4 hours. The warm reaction mixture was poured into ice/water (30 mL) and the resulting precipitate was collected via filtration, to give an orange solid (2.16 g, 95% yield) which was dried over P2O5. This was used without further purification.

Workup

  1. customThe warm reaction mixture
  2. filtrationthe resulting precipitate was collected via filtration

Sources & evidence

ORD record
ord-6488610044af4bbab7d88fa1d9163422
Source dataset
uspto-grants-2014_01
Patent number
US08624025B2

Reaction notes

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