HuagongsheHuagongshe Chemistry Print Report · For research reference only
Formamide → 4-Chloro-7-fluoro-6-nitroquinazoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Formamide | HCID 713 | — |
| Reactant | Nitric Acid | HCID 944 | — |
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | 4-Fluoroanthranilic acid | HCID 2724967 | — |
| Reactant | HCID 178518022 | HCID 178518022 | — |
| Reactant | HCID 178526403 | HCID 178526403 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-Chloro-7-fluoro-6-nitroquinazoline | HCID 10609358 | — |
| Product | HCID 87756995 | HCID 87756995 | — |
Reaction Steps
4-Chloro-7-fluor-6-nitroquinazoline was prepared as described in Mishani et al. (2005). In brief, 2-amino-4-fluorobezoic acid was reacted with formamide, at 160° C. for 3 hours. The resulting 7-fluoro-4-hydroxyquinazoline (Compound 22) was then reacted with a mixture of nitric acid and sulfuric acid, at 100° C., for 2 hours, to thereby obtain 7-fluoro-4-hydroxy-6-nitroquinazoline (Compound 23), which was thereafter reacted with thionyl chloride in DMF (reflux, 7 hours), to obtain 4-chloro-fluoro-6-nitroquinazoline (Compound 24, see, FIG. 3).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08461166B2 |
| Source dataset | uspto-grants-2013_06 |
| ORD ID | ord-6f2573759f40405990c81c5ffd7ef37e |
| Source note | uspto-grants-2013_06 |