Acetic Acid → 4(1H)-Quinazolinone
Reaction equation
Cl[C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][C:6](OC)=[C:7](OC)[CH:8]=2)[N:3]=1.CC(O)=[O:19]>[OH-].[Na+].C1COCC1>[CH:7]1[CH:6]=[CH:5][C:4]2[N:3]=[CH:2][NH:11][C:10](=[O:19])[C:9]=2[CH:8]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2,4-dichloro-6,7-dimethoxy-quinazoline (2.12 g, 8.20 mmol) in 1 M NaOH (50 mL) and THF (15 mL) was stirred at room temperature under an argon blanket for 23 hours. The solution was cooled to 0° C., then acidified to pH 5 with AcOH. The resulting solids were collected by vacuum filtration and dried in a vacuum oven at 70° C. overnight to provide Intermediate 8 as a pale yellow powder (2.02 g, 100%). 1H NMR (300 MHz, DMSO-d6) δ: 7.38 (s, 1H), 7.08 (s, 1H), 3.88 (s, 3H), 3.85 (s, 3H), 3.50–3.20 (br s, 1H).
Workup
- filtrationThe resulting solids were collected by vacuum filtration
- customdried in a vacuum oven at 70° C. overnight
Sources & evidence
- ORD record
- ord-e07b7f8a81c8479598e9ab442c1ea0df
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07022856B2
Reaction notes
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