1,2-Dichloroethane → Ammonia dichloromethane

Participants

Reaction Steps

A solution of the product of Example 9 (260 mg), 4-chloroaniline (180 mg), and acetic acid (0.06 mL) in DCE (3 mL) was treated with sodium triacetoxyborohydride (360 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (5 mL) and extracted with DCM (3×10 mL). The combined organic phases were dried (sodium sulfate) and evaporated. Chromatography of the residue (1-5% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (168 mg). 1H NMR (400 MHz, CDCl3): 7.25 (d, J=8.8 Hz, 2H), 7.10 (d, J=8.9 Hz, 2H), 6.87 (d, J=8.8 Hz, 2H), 6.54 (d, J=8.9 Hz, 2H), 4.21 (d, J=4.7, 2H), 3.99 (t, J=6.3 Hz, 2H), 2.52-2.38 (m, 6H), 1.99 (m, 2H), 1.64-1.57 (m, 4H), 1.49-1.42 (m, 2H).

Provenance & Evidence