ChemicalBook CAS DataBase List 3-Pyridinecarboxamide,2-(methylamino)-(9CI)

3-Pyridinecarboxamide,2-(methylamino)-(9CI) synthesis

5synthesis methods

Product Name:3-Pyridinecarboxamide,2-(methylamino)-(9CI)
CAS Number:103976-52-9
Molecular formula:C7H9N3O
Molecular Weight:151.17

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3-Pyridinecarboxamide,2-(methylamino)-(9CI)

103976-52-9
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Yield:103976-52-9 73%

Reaction Conditions:

with dihydrogen peroxide;potassium carbonate in dimethyl sulfoxide at 20; for 1 h;

Steps:

84.2 2-(Methylamino)pyridine-3-carboxamide

2-(Methylamino)nicotinonitrile (600 mg, 4.51 mmol), potassium carbonate (1.87 mg, 0.130 mmol) and hydrogen peroxide (0.1 mL) were dissolved in dimethylsulfoxide (10 mL), reacted for 1 hour at room temperature and quenched by the addition of water (10 mL).
The reaction solution was extracted with ethyl acetate (10 mL x 3), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure, and purified on a silica gel plate (1: 1 petroleum ether / ethyl acetate, R_f = 0.2) to give 2-(methylamino)pyridine-3-carboxamide (500 mg, white solid) with a yield of 73%. ¹H NMR: (400 MHz, DMSO-d₆) δ 8.45-8.40(br, 1H), 8.28(d, J = 2.0 Hz, 1H), 7.95-7.93(m, 2H), 7.35-7.30(br, 1H), 6.53(dd, J = 7.6, 2.0 Hz, 1H), 3.03(d, J = 4.8 Hz, 3H). MS-ESI calcd. [M + H]⁺ 152, found 152.

References:

EP3299371,2018,A1 Location in patent:Paragraph 0528; 0530

103976-61-0 Synthesis