Benzene → Methyl 6-aminoquinoline-5-carboxylate
Reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]=1[C:12]([OH:14])=[O:13].[CH:15]1C=CC=CC=1.[Si](C=[N+]=[N-])(C)(C)C>CO>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]=1[C:12]([O:14][CH3:15])=[O:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of Example 96A (0.43 g, 2.3 mmol), benzene (10 mL), and methanol (4 mL) was treated with TMSCHN2 (2.0 mL, 4.0 mmol, 2.0M solution in hexanes), stirred at room temperature for 90 minutes, quenched with glacial acetic acid, and concentrated. The residue was diluted with ethyl acetate, washed with saturated Na2CO3, dried (MgSO4), filtered, and concentrated to provide the desired product (0.401 g). MS (DCI) m/e 220 (M+NH4)+.