Nitric Acid → 7-[3-[4-[(4-Chlorophenyl)methyl]-1-piperazinyl]propoxy]-4-hydroxy-3-nitro-2H-1-benzopyran-2-one

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Reaction Steps

Fuming nitric acid (10 ml; d 1.52) was added dropwise over 15 mins to a cold (0° C.) stirred suspension of 1-(4-chlorobenzyl)-4-[3-(4-hydroxycoumarin-7-yloxy)propyl]piperazine (2.0 g) in chloroform (200 ml) and the mixture stirred for a further 1 hour at 0°. The solution which formed precipitated a yellow solid on addition of water which after filtration was washed with ethanol to give 2.62; (95%) of the dinitric acid salt of the title compound of m.p. 142°-144° (dec). νmax (mull) 2700 (br), 1740, 1615, 1525 cm-1. (Found; C, 45.87; H. 4.52; Cl, 5.66; N, 11.36; C23H24ClN3O6 2HNO3 requires; C, 46.05; H, 4.37; Cl, 5.91; N, 11.67%).

Provenance & Evidence