Hydrochloric Acid → HCID 11774917, compound

Participants

Reaction Steps

A solution of 3-(2-aminophenoxy)phthalic acid dimethyl ester (200 mg, 0.54 mmol) and 3-nitrobenzaldehyde (90 mg, 0.60 mmol) in toluen (20 ml) was refluxed for 30 hours with a Dean-Stark trap. The reaction mixture is cooled to room temperature and evaporated to dryness in vacuo. The residue was dissolved in methanol (5ml), sodium cyanoborohydride (100 mg, 1.58 mmol) was added, and pH adjusted to 4.5 by means of hydrogen chloride in ether. The mixture was stirred at room temperature for 20 hours, evaporated in dryness in vacuo, and partioned between methylene chloride (5 ml) and water (5 ml). The organic phase was isolated, dried over magnesium sulphate, and evaporated to dryness in vacuo. The crude compound was purified on silica gel (eluent: methylene chloride:ethyl acetate (95:5)) to give 4-[2-(3-nitrobenzylamino)phenoxy]phthalic acid dimethyl ester as a yellow oil (yield: 130 mg (55%). 1H—NMR (CDCl3) in ppm: δ 8.05-8.18 (2H,m); 7.84 (1H,d); 7.63 (1H,d); 7.50 (1H,t); 7.20 (1H,d); 6.9-7.1 (3H,m); 6.73 (1H,d.t.); 6.6 (1H,d.d.); 4.56 (1H,broad, s): 4.48 (2H,broad s); 3.9 (3H,s); 3.87 (3H,s). LC-MS: m/e 459 (M+Na), 437 (MH+).

Provenance & Evidence