Isopropylamine → 6-Isopropylamino-5-methyl-nicotinic acid isopropyl ester
Reaction equation
[CH:1]([O:4][C:5](=[O:14])[C:6]1[CH:11]=[C:10]([CH3:12])[C:9](Cl)=[N:8][CH:7]=1)([CH3:3])[CH3:2].[CH:15]([NH2:18])([CH3:17])[CH3:16]>O1CCOCC1>[CH:1]([O:4][C:5](=[O:14])[C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([NH:18][CH:15]([CH3:17])[CH3:16])=[N:8][CH:7]=1)([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 6-chloro-5-methyl-nicotinic acid isopropyl ester (200 mg, 0.936 mmol) in dioxane (5 mL) and isopropylamine (3 mL) is stirred in a sealed vial at 100° C. for 1 week. The solvent is evaporated and the residue dissolved in DCM (50 mL) and washed with sat. aq. NaHCO3 solution (20 mL). The org. extract is dried over MgSO4, filtered and concentrated. The crude product is purified on prep. TLC plates with heptane:EA 1:1 to give 6-isopropylamino-5-methyl-nicotinic acid isopropyl ester (137 mg) as a yellow oil; LC-MS: tR=0.68 min, [M+1]+=237.02.