Benzoic acid, 2-amino-5-iodo- → 6-Iodoquinazolin-4-one
Reaction equation
[I:1][C:2]1[CH:10]=[C:6](C(O)=O)[C:5]([NH2:11])=[CH:4][CH:3]=1.[CH:12]([O-])([O-])OC.[CH3:17][OH:18].[NH3:19]>>[I:1][C:2]1[CH:10]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:11]=[CH:12][NH:19][C:17]2=[O:18]Participants
Conditions
- Temperature
- 5 °C
Procedure
In a 200 mL volume stainless steel pressure-resistant vessel equipped with a thermometer, an pressure gauge, and a stirrer were placed 25.0 g (95 mmol) of 5-iodoanthranilic acid, 17.1 g (162 mmol) of methyl orthoformate, and 50 mL (349 mmol) of 15 wt. % ammonia methanol solution. The reaction was carried out at a temperature of 100-110° C. and a pressure of 0.5 MPa (gauge pressure) for 8 hours. After the reaction was complete, the reaction mixture was cooled to a temperature of 0-10° C. and placed under reduced pressure to distill ammonia off. The residual reaction mixture was then stirred at 0° C. for one hour. The precipitated solid was collected by filtration and dried, to obtain 24.3 g (isolated yield: 94%) of 6-iodoquinazolin-4-one as a pale gray crystalline product.
Workup
- customIn a 200 mL volume stainless steel pressure-resistant vessel equipped with a thermometer
- customwas carried out at a temperature of 100-110° C.
- distillationto distill ammonia off
- customThe residual reaction mixture
- filtrationThe precipitated solid was collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-be3a7839e24c43d7b4f4ec96fc640185
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07232903B2
Reaction notes
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