Hydrochloric Acid → N*1*-(8-Methoxy-2-methylquinolin-4-yl)-1-phenylethane-1,2-diamine

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Reaction Steps

2-(8-Methoxy-2-methylquinolin-4-ylamino)-2-phenylacetamide (example 74, 430 mg, 1.33 mmole) was suspended in tetrahydrofurane (20 mL) and BH3xSMe2 (2M in tetrahydrofurane) was added dropwise. The mixture was refluxed under stirring for 1 h and then stirred at RT for 12 hrs. The content of the flask was carefully mixed with 2N HCl and refluxed for 2 hrs. The reaction mixture was alkalized and extracted with dichloromethane. The organic phases were dried and concentrated. The residue thus obtained was purified using HPLC (RP-18, eluting with water/acetonitrile) to obtain the product (12%, 83 mg). ESI-MS [M+H]+=294.1 calculated for C22H21F6N3O5=293 g/mole

Provenance & Evidence