反应详情

A solution of methyl 1-(7-aminoquinazolin-4-yl)-5-methoxy-2-methylindol-3-ylacetate (0.5g.) in acetic acid (12 ml.) was treated with concentrated hydrochloric acid (1.5 ml.). The solution obtained was stirred at 0°-5° C during the addition, over 15 minutes, of a solution of sodium nitrite (0.15g.) in water (2 ml.). The dark red solution was added dropwise to a solution of cuprous chloride (0.2g.) in concentrated hydrochloric acid (5ml.) kept at room temperature. The mixture was then stirred for 1 hr. before addition of sufficient sodium acetate to adjust the pH of the mixture to 4-5. The mixture was then concentrated in vacuo and the residue treated with water (100ml.) and ethyl acetate (50ml.). The aqueous layer was extracted with ethyl acetate (2 × 30ml.) and the extracts washed with saturated sodium hydrogen carbonate solution (2 × 30ml.). After being washed with water (30ml.) and dried(Na2SO4), evaporation of the extracts in vacuo gave an oil, which slowly solidified to give methyl 1-(7-chloroquinazolin-4-yl)-5-methoxy-2-methyl-indol-3-ylacetate as a yellow solid, m.p. 111°-114° C.

1. customThe solution obtained
2. customkept at room temperature
3. concentrationThe mixture was then concentrated in vacuo
4. additionthe residue treated with water (100ml.) and ethyl acetate (50ml.)
5. extractionThe aqueous layer was extracted with ethyl acetate (2 × 30ml.)
6. washthe extracts washed with saturated sodium hydrogen carbonate solution (2 × 30ml.)
7. washAfter being washed with water (30ml.) and dried(Na2SO4), evaporation of the extracts in vacuo
8. customgave an oil, which