Nitric Acid → 7-Chloro-6-nitroquinazoline-2,4(1H,3H)-dione

HRID 2294181Notes

Reaction equation

HRID 2294181 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:13])[NH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:13])[NH:7][C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 2468587-Chloroquinazoline-2,4-diol

Product 1

HCID 3522687-Chloro-6-nitroquinazoline-2,4(1H,3H)-dioneYield 54%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

20 g (101.7 mmol) 7-chloro-1,2,3,4-tetrahydroquinazoline-2,4-dione were dissolved in 100 ml of conc. sulphuric acid and treated with 7 ml of conc. nitric acid. The mixture was heated to 100° C. for 10 min. After cooling the reaction mixture was poured on to ice-water. The precipitate was filtered off, dried in a high vacuum and recrystallized from acetic acid. 13.3 g (54%) of 7-chloro-6-nitro-1,2,3,4-tetrahydroquinazoline-2,4-dione were obtained as beige crystals;

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationThe precipitate was filtered off
  3. customdried in a high vacuum
  4. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-4015ce42e7c146b6bc0fa1097ac0cb5c
Source dataset
uspto-grants-1997_11
Patent number
US05688803

Reaction notes

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