Allyl bromide → HCID 57698807, compound

Participants

Reaction Steps

To a stirred solution of allyl bromide (39.7 ml, 459.18 mmol) and tert-butylnitrite (5.5 ml, 45.91 mmol) in acetonitrile (30 ml) was added methyl 6-nitroanthranilic acid (6.0 g, 30.61 mmol) portion-wise at room temperature and the mixture was further stirred for 1 h. The volatile components were evaporated under reduced pressure and the residue was diluted with water. The mixture was extracted with ethyl acetate (2×50 ml) and the combined organic extracts were washed with water and dried over anhydrous sodium sulfate. The residue obtained after evaporation of the solvent was purified by silica gel column chromatography using 5% ethyl acetate in petroleum ether as eluent to give 4.2 g of the product as a yellow oil; 1H NMR (δ ppm, CDCl3, 300 MHz): 7.99 (d, J=7.8, 1H); 7.58-7.46 (m, 2H); 5.93-5.80 (m, 1H), 5.15-5.03 (m, 2H); 3.93 (s, 3H); 3.46 (d, J=6.0, 2H).

Provenance & Evidence