Water → HCID 9869398, compound

Participants

Reaction Steps

The methyl benzoate (0.65 g) was dissolved in 10 mL 1:1 THF/MeOH, and this solution was treated with 2 mL 50% NaOH and 1 mL water and stirred at room temperature for 18 hours. When the starting material was no longer observed by mass spec, the mixture was concentrated, the solids were dissolved in ethyl acetate/water 1:1. The layers were separated, and the aqueous layer was extracted with 2×20 mL ethyl acetate. The organic layers were combined and washed with 10 mL 50% saturated NaCl, dried over MgSO4/Na2SO4, filtered, and concentrated. The residual oil was purified by column chromatography (MPLC, silica, gradient 98:2 to 80:20)(CH2Cl2/MeOH+1% NH4OH). Fractions containing the desired product were combined, concentrated, and dried in vacuo overnight to give 2-[2-(3,4-dichlorobenzylamino)-indan-5-ylamino]-5-nitro-benzoic acid (0.38 g, 60% yield). MS (APCI) m/z 470.0 (M+−1). CHN for (C23H19Cl2N3O4·CH2Cl2) calc: C, 55.58, H, 3.94, N, 8.31; found: C, 55.25, H, 3.88, N, 8.32.

Provenance & Evidence