Water → 3-(3-Aminonaphthalen-2-ylamino)propionic acid ethyl ester

Participants

Reaction Steps

A solution of 2,3-diaminonaphthalene (14.3 g, 90.4 mmol) and ethyl 3-bromopropionate (14 mL, 0.108 mol) in DMF (150 mL) was heated to 50° C. for 24 h. The reaction mixture was poured into water (600 mL) and the product was extracted into CH2Cl2 (2×200 mL). The combined organics were washed three times with water and dried over Na2SO4. The solvent was evaporated in vacuo and the resultant residue was purified by flash chromatography using 27% to 40% EtOAc in hexane as the eluant to give the product as a brown solid, 7.6 g (33%): MS m/z 259 (MH+); 1H NMR (DMSO-d6) δ 1.22 (t, 3H), 2.73 (t, 2H), 3.37-3.45 (m, 2H), 4.12 (q, 2H), 5.03 (br s, 2H), 5.09 (br t, 1H), 6.71 (s, 1H), 6.85 (s, 1H), 6.98-7.05 (m, 2H), 7.36-7.43 (m, 1H) and 7.47-7.53 (m, 1H).

Provenance & Evidence