2,2'-IMINODIBENZOIC ACID synthesis
- Product Name:2,2'-IMINODIBENZOIC ACID
- CAS Number:579-92-0
- Molecular formula:C14H11NO4
- Molecular Weight:257.24
Yield:579-92-0 100%
Reaction Conditions:
with copper(I) oxide;copper;potassium carbonate in N,N-dimethyl-formamide at 130; for 20 h;Inert atmosphere;
Steps:
1 Synthesis of 2,2 ‘-Iminodibenzoic acid
An oven dried 4000m1 four neck flask fitted with nitrogen inlet, condenser and overhead stiner was charged with 2-bromobenzoic acid (50.0g, 248.73 mmol), anthranilic acid (34.llg, 248.73mmol) and anhydrous potassium carbonate (77.35g, 559.65mmol). Air was replaced with nitrogen for 30 mi Anhydrous DMF (300m1) was added and stined. Copper powder (1.58g, 24.87mmol) was added followed by Cu20 (1.78g, 12.44mmol). The reaction mixture was heated to 130°C for 20 hrs. The reaction was stopped and cooled down to room temperature. Most of the DMF was evaporated off under reduced pressure. Water (500m1) was added to the residue and stined. The reaction mixture was acidified with aqueous HC1 to pH=4 which resulted in a grey precipitate. It was filtered and washed thoroughly with water (700m1 x3). LC-MS showed a mass for the desired product with a trace of unreacted anthranilic acid left. The grey solid was dried in an oven at 50°C under vacuum (63g, yield quantitative). The material was used for the next step without further purification.‘H-NMR (600MHz, THF-d8): 5= 11.4 (brs, 1H), 10.92(s, 1H), 7.97(d, 2H), 7.49(d, 2H), 7.33 (m, 2H), 6.85(m, 2H).
References:
CAMBRIDGE DISPLAY TECHNOLOGY LIMITED;SUMITOMO CHEMICAL CO., LTD;TARRAN, William;LEE, James;ISLAM, Nazrul WO2018/229491, 2018, A1 Location in patent:Page/Page column 21; 22
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