Sodium Hydroxide → HCID 13064663, compound
Reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH:11][CH:12]([CH3:14])[CH3:13].[OH-].[Na+]>CO>[Cl:10][C:8]1[CH:7]=[CH:6][C:5]([NH:11][CH:12]([CH3:14])[CH3:13])=[C:4]([CH:9]=1)[C:3]([OH:15])=[O:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 480 mg of 5-chloro-2-isopropylamino-benzoic acid methyl ester in methanol (5 ml) were added 3.16 ml of a 1N NaOH solution and the mixture was stirred for 4 d at RT. Then the reaction mixture was concentrated in vacuo and the remaining residue dissolved in water. The resulting solution was washed with ethyl acetate and then the pH was adjusted to 1 with 1N HCl solution and the mixture was extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and concentrated to give the title compound as an off-white solid (429 mg, 95%). NMR (CDCl3, 300 MHz): δ 1.27 (d, J=6.3 Hz, 6H), 3.70 (sept, J=6.3 Hz, 1H), 6.65 (d, J=9.1 Hz, 1H), 7.31 (dd, J=9.1 and 2.7 Hz, 1H), 7.92 (d, J=2.7 Hz, 1H).