Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ammonium Hydroxide | HCID 14923 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | 2-Amino-3-nitrobenzoic acid | HCID 219633 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 2-Amino-3-nitrobenzamide | HCID 10797476 | 89% |
Reaction Steps
To a solution of 2-amino-3-nitrobenzoic acid (prepared using the procedure as described in U.S. Pat. No. 6,737,421, EXAMPLE 2, part b) in dimethoxyethane (DME, 7.1 mL/g), was added thionyl chloride (1.33 equivalents). The mixture was stirred at 50° C. for 12 hours, cooled and slowly added to concentrated ammonium hydroxide (22 equivalents). The mixture was stirred at 50° C. for 2 hours, water was added, and the mixture was cooled and filtered. The solid was washed with water and isopropanol, and dried under vacuum to give the title compound (89% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07462724B2 |
|---|
| Source dataset | uspto-grants-2008_12 |
|---|
| ORD ID | ord-d001356034684bd9a49b875ee7e1bdd0 |
|---|
| Source note | uspto-grants-2008_12 |
|---|