N-bromobutanimide → N-[6-[4-(Cyanomethyl)-1-naphthalenyl]-2-pyridinyl]-2,2-dimethylpropanamide

Participants

Reaction Steps

To a 100 mL round-bottomed flask equipped with condenser and N2 inlet were added 1.21 g (3.795 mmol) N-t-butylcarbonyl-6-(4-methylnaphthalen-1-yl)-pyridin-2-ylamine, 810 mg (4.554 mmol) N-bromosuccinimide, 35 mL carbon tetrachloride, and 10 mg bis-(1-cyano-1-azo)-cyclohexane. The reaction was heated at reflux for a total of 8 hours as additional portions of initiator were added at 1, 2, and 4 hours. The reaction was cooled, filtered with carbon tetrachloride, and evaporated. The red oil, 2.5 g, was used directly.

Provenance & Evidence