Ammonia → 6,7-Dihydroxy-4(3H)-quinazolinone

HRID 1797883Notes

Reaction equation

HRID 1797883 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13]C)[N:9]=[CH:8][NH:7][C:6]2=[O:15].COC1C=CC=C2C=1C(OC)=NC(=O)N2.Br.N>>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[N:9]=[CH:8][NH:7][C:6]2=[O:15]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 260Hydrogen BromideHCID 69168165HCID 69168165, compoundHCID 1354950166,7-Dimethoxy-3H-quinazolin-4-one

Product 1

HCID 1357422586,7-Dihydroxy-4(3H)-quinazolinoneYield 84%

Conditions

Temperature
100 °C

Procedure

To 6,7-dimethoxy-4(3H)-quinazolinone, 10 (3.0 g, 14.5 mmol) was added 48% HBr (36 mL) and the solution was heated to reflux at 100° C. for 12 h. The reaction mixture was cooled to room temperature and the solids were filtered. The solid obtained was neutralized with aq. NH3 (pH=8) and the solution was filtered and washed with water and dried to give 6,7-dihydroxy-4(3H)-quinazolinone, 11 as a off-white crystalline solid (2.20 g, 84%).

Workup

  1. temperaturethe solution was heated
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationthe solids were filtered
  4. customThe solid obtained
  5. filtrationthe solution was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-cb1fc1fd7eca4765ae8b0bbc4d559e61
Source dataset
uspto-grants-2013_01
Patent number
US08343950B2

Reaction notes

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