Sodium Hydroxide → HCID 43198040, compound

Temperature

0 °C

(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).

1. customthe resulting reaction mixture
2. concentrationThe reaction mixture was concentrated on a rotary evaporator
3. washthe residue was washed with ether
4. concentrationthe combined ether layers were concentrated
5. temperaturethe resulting mixture was refluxed for 3 hours
6. temperaturethe resulting mixture was refluxed for 14 hours
7. temperatureAfter cooling to room temperature
8. extractionthe reaction mixture was extracted with hexane
9. dry with materialthe combined organic extracts were dried with K2CO3
10. concentrationconcentrated

ORD record

ord-62858b13e51b4f7ebcb38145333f2ad6

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08557853B2