[OH-].[NH4+:2].[NH3:3].C(O[C:7](OCC)(OCC)[CH2:8][CH3:9])C.[Cl:16][C:17]1[CH:18]=[C:19]([C:23](=O)[CH2:24][C:25]([O:27]CC)=O)[CH:20]=[CH:21][CH:22]=1>CO.C(O)C>[Cl:16][C:17]1[CH:18]=[C:19]([C:23]2[N:3]=[C:7]([CH2:8][CH3:9])[NH:2][C:25](=[O:27])[CH:24]=2)[CH:20]=[CH:21][CH:22]=1
To a solution of ammonium hydroxide (3 mL) and ammonia in methanol (7.0 N, 10 mL) in ethanol (6 mL) was added 1,1,1-triethoxypropane (6.2 g, 35.3 mmol) and ethyl 3-(3-chlorophenyl)-3-oxopropanoate (4.0 g, 17.6 mmol) dropwise as a solution in ethanol (10 mL). Once the addition was complete, ammonium hydroxide (10 mL) was added. The mixture was heated with stirring in a sealed flask at 60° C. overnight. After this time, the mixture was cooled to rt and concentrated. The residue was purified by column chromatography (silica, hexanes/DCM) to afford the title compound (0.250 g, 6%) as a white solid. MW=234.68. 1H NMR (CDCl3, 500 MHz) δ 8.03 (t, J=1.9 Hz, 1H), 7.86-7.82 (m, 1H), 7.46-7.38 (m, 2H), 6.73 (s, 1H), 2.80 (q, J=7.6 Hz, 2H), 1.42 (t, J=7.6 Hz, 3H); APCI MS m/z 235 [M+H]+.
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