Sodium Nitrite → Quinazoline-4,7-diol

HRID 1171627Notes

Reaction equation

HRID 1171627 reaction equation
N([O-])=[O:2].[Na+].N[C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:16])[NH:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1>O.S(=O)(=O)(O)O.O>[OH:2][C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:16])[NH:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 1354780317-Amino-quinazolin-4-ol

Product 1

HCID 135451644Quinazoline-4,7-diolYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 21910475Sulfuric acid hydrate (1:1)Solvent

Procedure

A solution of sodium nitrite (1.40 g, 20.32 mmol) in water (17 mL) was added dropwise to a cooled suspension of 7-aminoquinazolin-4-one (712 mg, 4.42 mmol) in sulfuric acid/water (4.4 mL, 18 mL), keeping the temperature at approx. 0° C. The mixture was stirred at room temperature for 2 hours, diluted with water (15 mL) and heated at reflux for 15 minutes. The cooled mixture was neutralized and the precipitate was collected via filtration, and purified by column chromatography (silica) using 10% methanol/ethyl acetate as the eluent. The combined fractions gave an orange solid (541 mg, 76%).

Workup

  1. customat approx. 0° C
  2. temperatureheated
  3. temperatureat reflux for 15 minutes
  4. filtrationthe precipitate was collected via filtration
  5. custompurified by column chromatography (silica)

Sources & evidence

ORD record
ord-7ff377bde948495d8feed388c77dff72
Source dataset
uspto-grants-2010_11
Patent number
US07829705B2

Reaction notes

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