Reaction SMILES: [Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([N:12]([CH3:27])[C:13](=[O:26])[CH2:14][C:15]([N:17]([CH2:24][CH3:25])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:16])[C:3]=1[C:4]([O:6]C)=O.[O-]CC.[Na+].O.Cl>C(O)C>[CH3:25][CH2:24][N:17]([C:15]([C:14]1[C:13](=[O:26])[N:12]([CH3:27])[C:8]2[CH:9]=[CH:10][CH:11]=[C:2]([Cl:1])[C:3]=2[C:4]=1[OH:6])=[O:16])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
Reactant: CCN(C(=O)CC(=O)N(C)c1cccc(Cl)c1C(=O)OC)c1ccccc1
Agent: CC[O-]
Agent: Cl
Agent: [Na+]
Solvent: CCO
Solvent: O
Product: CCN(C(=O)c1c(O)c2c(Cl)cccc2n(C)c1=O)c1ccccc1
Reaction time: 1 h
Yield: 79 %

Procedure:
To (9) (5 mmol) dissolved in dry ethanol (25 ml) at 5° C. was added sodium ethoxide (0.37 g, 5.2 mmol). The mixture was stirred at this temperature for 1 h, and then at room temperature under TLC control. After completion of the reaction (˜2-3 h) [if the reaction was not completed by this time, the mixture was further refluxed for an additional 1-2 h], water (100 ml) was slowly added followed by a drop-wise addition of 1.0 N hydrochloric acid (6 ml) with stirring. After 30 minutes at 5° C., the crystals were collected by filtration, washed with water, and dried at 40° C. under vacuum to give (1) in 79% yield with an assay of 98.6%. b). To a stirred solution of (9) (10 mmol) in anhydrous THF (50 ml) was added sodium methoxide (3.6 mmol as 0.5 M in MeOH) portion-wise under N2 atmosphere, and the resulting mixture was refluxed for 2 h. The mixture was cooled and the solvent was evaporated partially to afford a concentrated solution, containing the insoluble salt. This was dissolved in a mixture of methanol (30 ml), 10M NaOH (1.07 mL, 10.7 mmol), and water (15.0 ml). Then, 5M HCl (aq) (2.4 ml, 12.0 mmol) was added. The crystalline precipitate was collected, washed with cold methanol and dried to afford the desirable compound in 87% yield with an assay of 98.9%. c). Solution of (9) (10 mmol) in 50 ml of methanol was stirred in the presence of Amberlyst A-26 (OH− form) under TLC control. After completion of the reaction (˜15-16 h), 1 M NaOH (50 ml) was added and the mixture was stirred for 30 min at room temperature, then filtered. The pH of filtrate was adjusted to 6.5 with 2 M HCl, and the solution was filtered through Celite followed by acidification to pH 1.5 and stirring for 1-2 h at room temperature, and for 2-3 h at 5° C. The precipitated product was filtered, washed with cold methanol and dried under reduced pressure. 71% yield of product was obtained with an assay of 97.6% d). Dry MgCl2 (0.47 g, 5.0 mmol) was added to 5 mL of CH2Cl2, stirred and the mixture was cooled to 0-5° C. Pyridine (0.80 mL, 10.0 mmol) was added, and the cold mixture was stirred for 15 min Neat acid chloride (11) (5 mmol) was then slowly added. The cold reaction mixture was allowed to stir for 15 min. The reaction mixture was then warmed to room temperature and stirred under TLC control. After completion of the reaction (˜1 h) the mixture was quenched with ice-water. The pH of the filtrate was adjusted to 6.5 with 2 M HCl, and the solution was filtered through Celite followed by acidification to pH 1.5 and stirring for 1-2 h at room temperature, and for 2-3 h at 5° C. The precipitated product was filtered, washed with cold methanol and dried at reduced pressure. 64% yield of product was obtained with an assay of 90.8%