Tetrahydrofuran → HCID 18387238, compound

Participants

Reaction Steps

A THF (5 ml) solution of 5-(4-methylphenyl)-8-oxo-8H-pyrano[3,4-b]pyridine-6-carboxylic acid (150 mg) was dropwise added to a mixture of 3-bromopropylamine hydrobromide (1.5 g), triethylamine (2.0 ml) and methanol (5 ml), and stirred at room temperature for 2 hours. Then, the solvent was removed by distillation. Hydrochloric acid (10 ml) was added to the residue, stirred for 14 hours at room temperature and then concentrated. The resulting concentrate was adjusted the pH to 1 with 1 N-NaOH. The crystals thus precipitated were taken out by filtration and washed with water to obtain 7-(3-bromopropyl)-7,8-dihydro-5-(4-methylphenyl)-8-oxo-6-pyrido[3,4-b]pyridinecarboxylic acid as colorless crystals (131 mg). m.p. 194-196° C. (recrystallized from THF-isopropyl ether) NMR(200 MHz, CDCl3 -DMSO-d6) ppm: 2.30-2.60(2H,m), 2.42(3H,s), 3.54(2H,t,J=6.8 Hz), 4.29(2H,t,J=7.2 Hz), 5.42(1H,bs,--CO2H), 7.20-7.40(4H,m), 7.50(1H,m), 7.64(1H,d,J=8.0 Hz), 8.88(1H,m).

Provenance & Evidence