Potassium Nitrate → HCID 58124932, compound

Participants

Reaction Steps

To a solution of 35 g of 6-methoxy-3,4-dihydroisoquinoline-1-carboxylic acid ethyl ester in 250 ml of concentrated sulphuric acid was added, at 0° C., 21 g of KNO3 in portions over 5 min. The reaction mixture was stirred for 1 h and then poured with stirring onto 500 g of NaHCO3. The resulting mixture was diluted with 2 l of ice-water and the product was extracted into dichloromethane. The organic layer was washed with water, dried, concentrated and the residue was treated with diethyl ether, to provide 34 g of 6-methoxy-7-nitro-3,4-dihydroisoquinoline-1-carboxylic acid ethyl ester, 5d MS-ESI: [M+1] 279.07. NMR (CDCl3) δ 1.42 (t, 3, OCH2CH3), 2.82 (t, 2, CH2), 3.94 (t, 2, CH2), 4.46 (q, 2, OCH2CH3), 6.92 and 8.44 (2×s, 2, Ar—H).

Provenance & Evidence