Ethanol → 3-Amino-6-chloropyridine-2-carboxamide

반응식

[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]=1

참가 물질

반응물 3

HCID 702Ethanol

HCID 24479Stannous Chloride

HCID 133817056-Chloro-3-nitropyridine-2-carbonitrile

생성물 1

HCID 107497043-Amino-6-chloropyridine-2-carboxamide

반응 조건

온도: 90 °C

실험 절차

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).