Ethanol → 3-Amino-6-chloropyridine-2-carboxamide
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([N+:10]([O-])=O)=[CH:4][CH:3]=1.Cl[Sn]Cl.CC[OH:18]>>[NH2:10][C:5]1[C:6]([C:8]([NH2:9])=[O:18])=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1Participants
4
Conditions
- Temperature
- 90 °C
Procedure
6-chloro-3-nitro-pyridine-2-carbonitrile (100 mg, 0.54 mmol) is taken up in EtOH (1 mL), combined with SnCl2 (413 mg, 2.18 mmol) and heated to 90° C. for 3 h. Then the solvent is removed, the residue is taken up in ethyl acetate and first of all washed with NaHCO3 to pH 7, then washed with NaOH (2 M) to pH 8-9. Then the residue is filtered through Celite®, the filtrate is extracted again with ethyl acetate and the combined organic phases are dried on Na2SO4. The solvent is eliminated in vacuo and 3-amino-6-chloro-pyridine-2-carboxylic acid amide is obtained (HPLC-MS: tRet.=0.78 min, MS(M+H)+=172, method LCMSBAS1).