Cl.[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([NH2:12])[C:8]=1[C:9]([OH:11])=[O:10].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)(O)[O-].[K+].[Cl-].[Na+]>CN(C)C=O>[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([NH2:12])[C:8]=1[C:9]([O:11][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10]
Under a nitrogen atmosphere a solution of 6.4 grams (0.031 mole) of 6-chloroanthranilic acid hydrochloride (prepared as in Example 3, Step B), 3.9 grams (0.031 mole) of benzyl chloride, and 6.2 grams (0.062 mole) of potassium bicarbonate in 100 mL of dimethylformamide was stirred at ambient temperature for about 48 hours. After this time the reaction mixture was poured into 250 mL of an aqueous solution saturated with sodium chloride. The mixture was extracted with three 250 mL portions of diethyl ether. The combined extracts were washed with one 250 mL portion of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished using 20% ethyl acetate in heptane. The appropriate fractions were combined and concentrated under reduced pressure to yield 6.4 grams of phenylmethyl 6-chloroanthranilate. The nmr spectrum was consistent with the proposed structure.
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