Water → 2-Amino-3-nitrobenzamide
Reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)(Cl)=O.[OH-].[NH4+:19].O>C(COC)OC>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:19])=[O:5]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
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).
Workup
- temperaturecooled
- stirringThe mixture was stirred at 50° C. for 2 hours
- temperaturethe mixture was cooled
- filtrationfiltered
- washThe solid was washed with water and isopropanol
- customdried under vacuum
Sources & evidence
- ORD record
- ord-10723559ed7945fd884e11a711969e85
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07595406B2
Reaction notes
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