Sodium Hydroxide → HCID 43198040, compound

Participants

Reaction Conditions

Reaction Steps

(5-Methyl-thiophen-2-yl)-m-tolyl-methanone (5.00 g, 23.12 mmol) was mixed with methoxylamine hydrochloride (3.00 g, 35.92 mmol) in pyridine and the resulting reaction mixture was stirred for 14 hours. The reaction mixture was concentrated on a rotary evaporator, the residue was washed with ether and the combined ether layers were concentrated. The residue was dissolved in BH3.THF (100.00 mL, 1.0 M in THF, 0.10 mol) and the resulting mixture was refluxed for 3 hours. The reaction mixture was then cooled to 0° C., 20% NaOH was added and the resulting mixture was refluxed for 14 hours. After cooling to room temperature, the reaction mixture was extracted with hexane and the combined organic extracts were dried with K2CO3 and concentrated to give the desired title amine. Spectroscopic data: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.26 (s, 3H) 2.32 (s, 3H) 3.30 (br s, 2H) 5.14 (s, 1H) 6.48-6.58 (m, J=14.36 Hz, 1H) 6.58-6.67 (m, 1H) 6.93-7.08 (m, 1H) 7.11-7.27 (m, 3H).

Provenance & Evidence