Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 22117812, compound

Temperature

0 °C

3-Bromo-4-chlorobenzoic acid (1.0 g, 4.24 mmol, 1.0 eq) was dissolved in dry DMF and stirred for 10 minutes. The solution was cooled to 0° C. and treated with N,O-dimethyl hydroxylamine hydrochloride (0.828 mg, 8.48 mmol, 2.0 eq), 1-hydroxybenzotrizole (860 mg, 6.36 mmol, 1.5 eq), N,N-diisopropyl ethylamine (820 mg, 6.37 mmol, 1.5 eq), and EDC HCl (1.2 g, 6.37 mmol, 1.5 eq). The reaction mixture was stirred for 12 h, evaporated under reduced pressure and diluted with water (25 mL). The aqueous layer was extracted with ethyl acetate. The organic layer was dried under anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel (60-120) eluting with 5-10% ethyl acetate/hexane to afford the desired product (1 g, 85%). 1H NMR (400 MHz, CD3OD) δ 3.34 (s, 3H), 3.57 (s, 3H), 7.47-7.49 (d, 1H), 7.71-7.74 (d, 1H), 7.85-7.88 (d, 1H). MS (ESI): 278.2 (M+).

1. stirringThe reaction mixture was stirred for 12 h
2. customevaporated under reduced pressure
3. additiondiluted with water (25 mL)
4. extractionThe aqueous layer was extracted with ethyl acetate
5. customThe organic layer was dried under anhydrous Na2SO4
6. concentrationconcentrated under vacuum
7. customThe residue was purified by flash column chromatography on silica gel (60-120)
8. washeluting with 5-10% ethyl acetate/hexane

ORD record

ord-1df1f6a8ea064fa9b3a7a63d3a463fbb

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501992B2