[C:1](#N)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH:10]1([Mg]Br)[CH2:14][CH2:13][CH2:12][CH2:11]1.Cl.[OH-:18].[Na+].O>C(OCC)C.O.C(OCC)(=O)C>[NH2:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:18]
To a solution of anthranilonitrile (15.0 g) in diethyl ether (600 mL) was added a solution of 2.0 M cyclopentylmagnesium bromide in diethyl ether (159 mL) at 0° C. under nitrogen. The mixture was stirred at room temperature overnight (20 hours). 500 ml of 5 N HCl in H2O was added very slowly at 0° C. The mixture was stirred at room temperature for 1 hour. The aqueous layer was neutralized with 50% NaOH/H2O to pH=12. 2×500 mL of ethyl acetate was used to extract the aqueous layer. The combined organic layers were dried over Na2SO4. The solvent was removed to give the crude product 22.5 g (93.6% yield). H1NMR (CDCl3): δ6.62-7.82 (m, 4H), 3.64-3.78 (m, 1H), 1.50-1.96 (m, 8H).
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