Pyridine → 4-nitro-N-(pyridin-4-ylmethyl)benzamide

Participants

Reaction Steps

to a solution of 4-(aminomethyl)pyridine (12.9 ml, 127 mmol) and pyridine (51.4 ml, 636 mmol) in 150 mL dichloromethane cooled by an ice bath was added 4-nitrobenzoyl chloride (24.8 g, 133 mmol) all at once, generating a dark red reaction solution. LC-MS at 5 minutes indicated reaction complete and the desired product predominated. The reaction was stirred at room temperature overnight then the solid collected by filtration. LC-MS indicated that the filtrate was desired product. The solid was washed with 5% aqueous sodium hydroxide solution until aqueous layer was alkaline then the solid collected by filtration. The solid was dried overnight in a vacuum dessicator over P2O5 (28.4 g, 87%). ESI+ m/z=258.1 [MH]+.

Provenance & Evidence