Diisopropylamine → HCID 19594770, compound

Participants

Reaction Conditions

Reaction Steps

Prepare LDA reagent by combining 4.1 mL n-butyl lithium (2.5 M in hexane) and 1.4 mL diisopropylamine dropwise, under argon in 40 mL tetrahydrofuran (THF) at -50° C. Allow the reaction to warm to 0° C. and dropwise add N,N-diethyl-2'-isopropoxy-6-methoxy-biphenyl-2-carboxamide (1.4 g, 4.1 mmole) dissolved in THF (15 mL) while stirring. Maintain the temperature at 0° C. for 10 minutes, then allow the reaction to obtain room temperature, as the color slowly changes to yellow. Heat the reaction at reflux for about 2 hours and observe the yellow solution darken. Quench the reaction with saturated ammonium chloride, extract with ether and wash the organic layer with water. Recrystalize from ether/methanol to obtain an orange solid of the title compound (0.34 g, 1.3 mmole, 31%). m.p. 118-120° C.

Provenance & Evidence