Ammonia → HCID 68886568, compound

Participants

Reaction Steps

A N,N-dimethylacetamide (110 mL) solution of the 9-chlorobenzo[g]quinoline (10.8 g, 55.27 mmol) from Step 2, Pd2(dba)3 (1.02 g, 0.02 eq), dppf (1.25 g, 0.04 eq), Zn powder (0.457 g, 0.13 eq) and Zn(CN)2 (3.97 g, 0.61 eq) was heated at 150° C. for 8 h in a sealed tube. The mixture was then poured into aqueous ammonia (2 N, 500 mL). The resulting yellow precipitate was collected by filtration and redissolved in CH2Cl2. The filtrate was extracted once with ethyl acetate. The organic phase was combined, dried over MgSO4, filtered and concentrated to ˜10% of original solvent volume. Pure 9-cyanobenzo[g]quinoline (10.3g, 91%) was obtained by filtration. MS Found: (M+H)+=205.

Provenance & Evidence