2-PHENYLAMINO-3-NITROBENZOIC ACID synthesis
- Product Name:2-PHENYLAMINO-3-NITROBENZOIC ACID
- CAS Number:54420-95-0
- Molecular formula:C13H10N2O4
- Molecular Weight:258.23
Yield:54420-95-0 98%
Reaction Conditions:
with copper diacetate;potassium carbonate at 160; for 1 h;Inert atmosphere;Ullmann Condensation;
Steps:
5.8.1 Step 1: Synthesis of 6-nitrodiphenylamine-2-carboxylic acid by Ullmann reaction.
Step 1:
Synthesis of 6-nitrodiphenylamine-2-carboxylic acid by Ullmann reaction.
Aniline (2.9mL, 31.75mmol) and 2-chloro-3-nitrobenzoic acid (1g, 4.96mmol) were charged to a 50mL rbf equipped with a reflux condenser and nitrogen bubbler.
To the resulting mixture was added copper (II) acetate (45mg) followed by anhydrous potassium carbonate (789mg, 5.71mmol).
The reaction mixture was heated to 160°C for 1 hour, and then cooled to room temperature.
The residue was diluted with water and acidified with an aqueous hydrochloric acid 2M solution until pH of 2 was reached.
The mixture was triturated until a green powder appeared.
The solid was filtered, washed with an excess of water to remove aniline and allowed to suck dry over 1 hour. 6-Nitrodiphenylamine-2-carboxylic acid was obtained as a green powdery solid (1.26g, 98%).
Analyses by 1H NMR and LCMS conformed to structure.
References:
EP1940965,2014,B1 Location in patent:Paragraph 0105-0106
