Acetic Acid → HCID 68810009, compound

Participants

Reaction Steps

A stirred mixture of 2-amino-5-methoxybenzoic acid (4 g), trimethylorthoformate (3.93 ml), and acetic acid (0.137 ml) in toluene (100 ml) was heated under reflux for 2 hours. 3-amino-4-methyl-N-(1-methylcyclopropyl)benzamide (4.39 g) was added to the reaction mixture and stirring continued in refluxing toluene for 16 hours. The reaction mixture was allowed to cool and then was diluted with ethyl acetate. The organic solution was then washed with 1N HCl solution, 2N NaOH solution (×2), brine, dried (magnesium sulfate) and concentrated to a cream coloured solid. The solid was dissolved in ethyl acetate and the insoluble material removed by filtration. Iso-hexane was added to the filtrate and concentrated to give 3-(6-methoxy-4-oxoquinazolin-3(4H)-yl)-4-methyl-N-(1-methylcyclopropylbenzamide (4.3 g); NMR Spectrum: (DMSOd6) 0.59 (m, 2H), 0.72 (m, 2H), 1.35 (s, 3H), 2.12 (s, 3H), 3.89 (s, 3H), 7.50 (m, 2H), 7.56 (m, 1H), 7.72 (d, 1H), 7.83 (s, 1H), 7.88 (d, 1H), 8.17 (s, 1H), 8.63 (s, 1H); Mass Spectrum: M+Na+ 486.

Provenance & Evidence