2-Hydrazinylisonicotinohydrazide synthesis

Yield:89465-51-0 90%

Reaction Conditions:

with hydrazine hydrate in ethanol;water at 160; under 7500.75 - 11251.1 Torr; for 1.5 h;Microwave irradiation;

Steps:

2-Hydrazinylpyridine-4-carbohydrazide (2a).

Ethyl 2-chloroisonicotinate (740 mg,4.00 mmol), hydrazine hydrate (88% solution in water, 2.3 mL, 40.0 mmol), and ethanol(0.7 mL) were combined in a 30 mL G30 vial and covered with a septum. The vial wasplaced in a Monowave 300 microwave reactor, and the mixture was heated to 160 Cover the course of 5 min (power did not exceed 135 watts), after which this temperaturewas maintained for 1.5 h (controlled by IR sensor, MW power within 10 watts, 10-15 barpressure). The resulting mixture was poured into water (40 mL) and filtrated. The resultingprecipitate was washed with water several times (2 30 mL). It was recrystallized fromethanol to afford 2a as a pale-yellow solid, m.p. 171-172 C (ethanol); yield 601 mg(3.60 mmol, 90%). Rf 0.16, EtOAc/Et3N (20:0.1: v/v). 1H-NMR (400 MHz, DMSO-d6) 9.83(br.s, NH, 1H), 8.03 (dd, J = 5.3, 0.8 Hz, 1H), 7.61 (br.s, NH, 1H), 7.07 (t, J = 1.1 Hz, 1H),6.84 (dd, J = 5.2, 1.5 Hz, 1H), 4.51 (br.s, NH, 2H), 4.15 (br.s, NH, 2H). 13C-NMR (101 MHz,DMSO) 164.9, 162.5, 147.9, 141.5, 109.4, 104.3. FTIR (ZnSe) (cm1): 3232, 2925, 2858,1739, 1652, 1619, 1556, 1462, 1250, 1103, 1055, 874. HRMS (ES TOF, m/z) calculated forC6H9N5NaO+ ([M + Na]+): 190.0694, found: 190.0699 (2.9 ppm).

References:

Aksenov, Alexander V.;Kirilov, Nikita K.;Aksenov, Nicolai A.;Aksenov, Dmitrii A.;Sorokina, Elena A.;Lower, Carolyn;Rubin, Michael [Molecules,2021,vol. 26,# 18,art. no. 5692]