HCID 10346280, compound → HCID 9979116, compound

Participants

Reaction Steps

A mixture of N,O-bis(acetonylacetyl)-3-(9-acridinylamino)-5-hydroxymethylaniline (423 mg, 0.83 mmol) in methanolic sodium methoxide [prepared from sodium (15 mg, 0.65mmol) in MeOH (15 mL)] is stirred at room temperature for 2 days. The mixture is passed through an ion-exchange resin (Dowex 50 in pyridine form). The product is eluted with a mixture of pyridine/H2O (v/v 1:1). The combined eluate is evaporated in vacuo to dryness. The product is purified by chromatography (SiO2, CHCl3 /MeOH, v/v 15:1) to give N-acetonylacety-3-(9-acridinylamino)-5-hydroxymethylaniline, 217 mg (64.0%), mp 197°-199° C. 1H-NMR (DMSO-d6): δ 2.10 (3H, s, COCH3), 4.35 (2H, broad singlet, CH2 --OH), 6.42 (1H, broad singlet, ArH), 6.90 (1H, broad singlet, ArH), 6.89-7.18 (2H, m, ArH), 7.19 (1H, broad singlet, ArH), 7.50-7.76 (4H, m, ArH), 8.30-8.48 (2H, m, ArH, 9.76 (1H, s, NH). Analyses: Calculated for C25H23N3O3 : C, 72.62; H, 5.61; N, 10.16. Found: C, 72.53; H, 5.46; N, 9.99.

Provenance & Evidence