Benzyl Alcohol → Methyl 6-amino-4-methylnicotinate

Reaktionsgleichung

[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=1.[C:12]1(CO)C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C>>[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]([O:11][CH3:12])=[O:10])=[CH:4][N:3]=1

Komponenten

Edukt 3

HCID 244Benzyl Alcohol

HCID 167693Trimethylsilyldiazomethane

HCID 99641496-Amino-4-methylnicotinic acid

Produkt 1

HCID 9877474Methyl 6-amino-4-methylnicotinate

Versuchsvorschrift

A mixture of 2-amino-5-carboxy-4-methylpyridine (100 mg, 0.657 mmol) in 7:3 benzene-methanol (4 mL) was treated with (trimethylsilyl)diazomethane (2M solution in hexanes, 0.33 mL, 0.66 mmol). The mixture was evaporated and the residue chromatographed on silica gel eluting with 25% acetone/hexane to afford pure title compound; yield 88 mg (81%).