Sulfuric acid magnesium salt (1:1) → HCID 18617552, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3.29 g (15.8 mmol) 5-(2-chloroethyl)indole-3-carboxaldehyde (reference example 5), 1.15 g (16.6 mmol) hydroxylamine hydrochloride, 6.27 g (52.1 mmol) magnesium sulfate, and 0.601 g (3.16 mmol) p-toluenesulfonic acid monohydrate in 10 mL DMF is heated to 150° C. for 30 minutes. The reaction mixture is azeotroped with toluene, and the resulting residue chromatographed (2:1, then 1:1 hexane:ethyl acetate) to provide 3.08 g of product as a white solid in 95% yield. 1H NMR (CDCl3): δ 3.20 (2H, t, J=7 Hz), 3.77 (2H, t, J=7 Hz), 7.21 (1H, dd, J=8, 1 Hz), 7.43 (1H, d, J=8 Hz), 7.63 (1H, s), 7.73 (1H, d, J=3 Hz), 8.66 (1H, br). MS (EI) m/z 204, 206 (M[35Cl, 37Cl])+, 155 (M−CH2Cl)+.

Provenance & Evidence