PYRIDINE-2-CARBOXYLIC ACID (2-AMINO-PHENYL)-AMIDE synthesis
- Product Name:PYRIDINE-2-CARBOXYLIC ACID (2-AMINO-PHENYL)-AMIDE
- CAS Number:90209-81-7
- Molecular formula:C12H11N3O
- Molecular Weight:213.24
794574-51-9
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Yield:90209-81-7 87%
Reaction Conditions:
with ammonium hydroxide;potassium phosphate;copper(II) bis(trifluoromethanesulfonate);vasicine in ethanol at 70; for 12 h;Sealed tube;regioselective reaction;Ullmann Condensation;
Steps:
General procedure for synthesis of 2-aminoanilides 3
General procedure: To a stirred solution of theo halobenzanilides 1 (1 mmol), Cu( 2 (18 mg, 0.05 mmol),vasicine (19 mg, 0.1 mmol) and K 3 PO 4 (425 mg, 2 mmol), 25% wt ammonia (1 mL) and EtOH (4mL) in a sealed tube at 70 o C for 8 12 h. After cooled to room temperature, the mixture wasconcentrated in vacuo and purified by column chromatography (DCM) to afford respective products.Compound 3a: 1 H NMR (400MHz, DMSO d6) δ : 9.68 (s, 1H), 7.99 (d, J =7.2 Hz, 2H), 7.49-7.59(m, 3H), 7.18 (d, J =7.5 Hz, 1H), 6.96-7.00 (m, 1H), 6.79 (dd, J =8.0, 1.3 Hz, 1H), 6.59-6.63 (m,1H), 4.90 (s, 2H); 13 C NMR (100MHz, DMSO d6) δ : 165.83, 143.61, 135.13, 131.84, 128.75,128.23, 127.16, 126.96, 123.84, 116.77, 116.63.
References:
Tang, Yan-Ling;Li, Mei-Ling;Gao, Jin-Chun;Sun, Yun;Qu, Lu;Huang, Feng;Mao, Ze-Wei [Tetrahedron Letters,2021,vol. 69,art. no. 153001] Location in patent:supporting information
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