HCID 15434654, compound → HCID 9952326, compound

Participants

Reaction Steps

A suspension of methyl 4-bis(2'-chloroethyl)amino-3-octoxybenzoate (1.8 g, 4.5 mmol) in concentrated HCl (37% w/w in H2O, 50 mL) was heated to refluxing under N2 for 0.5 hour. The reaction mixture was treated with ice/H2O (100 mL), extracted with chloroform (3×50 mL). The organic extract was concentrated to give a brown oil. Flash chromatographic purification (silica gel, 2% methanol in chloroform) gave the product 4-bis(2'-chloroethyl)amino-3-octoxybenzoic acid as an off-white solid (1.58 g, 88%). 1H NMR (300 MHz, CDCl3): 7.67 (dd, J=8.1, 1.5 Hz, 1H), 7.56 (d, J=1.5 Hz, 1H), 6.93 (d, J=8.4 Hz, 1H), 4.40 (d, J=6.6 Hz, 2H), 3.65 (m, 8H), 1.85 (J=7.8 Hz, 2H), 1.35 (m, 10H), 0.90 (t, J=6.6 Hz, 3H). ESMS calcd (C29H29Cl2NO3): 389.2; found: 390.2 (M+H)+.

Provenance & Evidence