Trimethylsilyldiazomethane → HCID 68862597, compound
Reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]([OH:14])=[O:13].[CH3:15][Si](C=[N+]=[N-])(C)C>C1C=CC=CC=1.CO>[CH3:15][C:11]1[C:2]([NH2:1])=[C:3]([C:12]([OH:14])=[O:13])[C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Amino-1-naphthoic acid (3.21 g, 17.2 mmol) in 4:1 benzene/CH3OH (125 mL) was treated with trimethylsilyldiazomethane (9.0 mL, 18.0 mmol, 2.0M solution in hexanes), stirred for 2.5 hours, quenched with acetic acid (0.5 mL), and concentrated. The concentrate was purified by flash column chromatography (4:1 hexanes/ethyl acetate) to provide the desired compound (3.25 g). MS (ESI(+)) m/e 202 (M+H)+; (ESI(−)) m/e 200 (M−H)−.