Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86598745, compound

Participants

Reaction Conditions

Reaction Steps

4-Phenyl-8-(trifluoromethyl)quinoline-3-carboxylic acid (6.19 g, 19.51 mmol) was taken into DMF (75 mL) and cooled to 0° C. Then PyBOP (10.66 g, 20.49 mmol) was added followed by N,O-dimethylhydroxylamine hydrochloride (2.09 g, 21.46 mmol) and diisopropylethylamine (8.50 mL, 48.78 mmol). The reaction was stirred for 3 hours allowing to warm to room temperature during that time. The reaction was poured into water and extracted with ethyl acetate. The combined organics was washed with water, half-saturated brine and then dried over magnesium sulfate. Purification was carried out via column chromatography using 30% ethyl acetate in hexane as the eluent to yield the desired compound as a white solid (6.37 g, 90.6%). MS (ESI) m/z 361 ([M+H]+); Anal. Calcd for C19H15F3N2O2.0.15H2O: C, 62.86; H, 4.25; N, 7.72. Found: C, 62.89; H, 4.14; N, 7.55.

Provenance & Evidence