Dimethylacetamide → 1-Oxo-1,2,3,4-tetrahydroisoquinoline-7-carbonitrile

Participants

Reaction Conditions

Reaction Steps

7-Iodo-3,4-dihydro-2H-isoquinolin-1-one (I-32b: 200 mg, 0.7326 mmol) in DMA (1 mL) was added to a stirred solution of Pd(dba)3 (4.02 mg, 0.0043 mmol), Zn dust (1.9 mg, 0.0293 mmol), Dppf (7.77 mg, 0.0095 mmol) in DMA (1 mL) previously degassed with argon for 15 mins. The reaction mixture was stirred for 5 mins. This was followed by the addition of Zn(CN)2 (51.6 mg, 0.4395 mmol) and the resulting mixture was heated to 120° C. for 4 hrs. The reaction was monitored by TLC (80% ethylacetate). The reaction mixture was diluted with ethylacetate and washed with 2N NH4OH solution. The organic layer was dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (70% ethylacetate in hexane) afforded 80 mg of the product (63.48% yield).

Provenance & Evidence