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ChemicalBook CAS DataBase List 6-HYDRAZINONICOTINIC ACID

6-HYDRAZINONICOTINIC ACID synthesis

4synthesis methods
5326-23-8 Synthesis
6-Chloronicotinic acid

5326-23-8
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6-HYDRAZINONICOTINIC ACID

133081-24-0
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Yield:133081-24-0 96%

Reaction Conditions:

with hydrazine hydrate at 100; for 4 h;Inert atmosphere;

Steps:


6-Chloronicotinic acid (0.30 g; 1.9 mmol) was added to a64% hydrazine monohydrate solution (2 mL, 26 mmol) andplaced at 100°C for 4h. Thereafter, the reaction mixtureturned brown and was concentrated to dryness. The residuewas dissolved in water and pH adjusted to 5.5 with concentratedHCl. A precipitate was formed, filtered and washedwith ethanol, then ether to give a yellow solid (0.346 g,96%). Mp = 292-293°C. IR (ATR, cm-1) 3210; 3058; 3039;1696; 1636; 1613; 1536-1444; 1170; 757; 736. 1H NMR(DMSO-d6) 8.63 (s, 1H); 8.07 (d, 1H, J= 9 Hz); 6.94 (d,1H, J = 9 Hz). 13C NMR (DMSO-d6) 167.2; 159.61;140.9; 119.9; 110.6. HRMS (ESI+) [M]+: 153.0531 observed,153.0538 Calcd for C6H7N3O2.

References:

Joyard, Yoann;Bischoff, Laurent;Levacher, Vincent;Papamicael, Cyril;Vera, Pierre;Bohn, Pierre [Letters in Organic Chemistry,2014,vol. 11,# 3,p. 208 - 214]

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