4-(2-Chloroethyl)morpholine → 7-(2-Morpholinoethoxy)naphthalene-2-sulfonic acid

Participants

Reaction Steps

Following a procedure analogous to that for the synthesis of Intermediate 26B, sodium 7-oxidonaphthalene-2-sulfonate (Pfaltz and Bauer, 200 mg, 0.75 mmol) and 4-(2-chloroethyl)morpholine (223 g, 1.49 mmol) were converted to the title compound (113 mg, 45%). 1H NMR (DMSO-d6) δ 9.90 (br s, 1H), 8.10 (s, 1H), 7.86 (d, J=8.8 Hz, 1H), 7.80 (d, J=8.4 Hz, 1H), 7.58 (dd, J=8.1, 1.3 Hz, 1H), 7.49 (d, J=1.8 Hz, 1H), 7.24 (dd, J=8.7, 2.3 Hz, 1H), 4.48 (br s, 2H), 3.99 (br s, 2H), 3.65 (br s, 4H), 3.26 (br s, 4H); MS (ESI+) m/z 336.3 (M+H)+.

Provenance & Evidence