Diiodomethane → 2-Iodo-4-methyl-5-nitropyridine

反応式

[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4](N)[CH:3]=1.N(OCCC(C)C)=O.[I:20]CI>>[I:20][C:4]1[CH:3]=[C:2]([CH3:1])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=1

参加物

反応物 3

HCID 6346Diiodomethane

HCID 8053Isoamyl Nitrite

HCID 2431652-Amino-4-methyl-5-nitropyridine

生成物 1

HCID 230701672-Iodo-4-methyl-5-nitropyridine収率 28%

実験手順

To a solution of 4-methyl-5-nitro-2-pyridinamine (12 g, 78.35 mmol) in diiodomethane (100 mL) was added isoamyl nitrite (22 mL, 160.4 mmol) at rt. After stirring for 30 min, the reaction was kept at 80° C. for 2 hr. The reaction was cooled and concentrated; but most of the diiodomethane remained. The crude mixture was loaded into column directly and eluted with 10% of EtOAc in hexane, and 2-iodo-4-methyl-5-nitropyridine (5.7 g, 28%) was obtained as a yellow solid after the removal of solvents under reduced pressure.