反应详情

温度

20 °C

A suspension of 7-fluoro-6-nitroquinazolone (2.40 g, 11.48 mmol) in neat SOCl2 (25 mL) containing 2 drops of DMF was refluxed for 3 hours until it became clear. The excess SOCl2 was then removed in vacuo and dry benzene was added to the residue and then distilled under reduced pressure to remove all traces of SOCl2 giving crude 4-chloro-7-fluoro-6-nitroquinazoline, which was dissolved in dry CH2Cl2 (50 mL) and added to a stirred solution of m-toluidine in isopropanol (i-PrOH) (30 mL). The reaction mixture was stirred at 20° C. for 30 minutes and then hexane (200 mL) was added to precipitate the product as the HCl salt. The precipitate was filtered, washed with hexane, and then dissolved in MeOH/H2O (4:1, 150 mL) with gentle warming. Excess Et3N was then added to the solution followed by water (400 mL) to precipitate the product as the free base which was then filtered, washed with water and dried under reduced pressure to give 7-fluoro-4-[(3-methylphenyl)-amino]-6-nitroquinazoline (3.01 g, 88%) as a yellow powder, mp (CH2Cl2/hexane) 191-192° C.

1. temperaturewas refluxed for 3 hours until it
2. customThe excess SOCl2 was then removed in vacuo and dry benzene
3. additionwas added to the residue
4. distillationdistilled under reduced pressure
5. customto remove all traces of SOCl2 giving crude 4-chloro-7-fluoro-6-nitroquinazoline, which
6. dissolutionwas dissolved in dry CH2Cl2 (50 mL)
7. additionadded to a stirred solution of m-toluidine in isopropanol (i-PrOH) (30 mL)
8. additionhexane (200 mL) was added
9. customto precipitate the product as the HCl salt
10. filtrationThe precipitate was filtered
11. washwashed with hexane
12. dissolutiondissolved in MeOH/H2O (4:1, 150 mL) with gentle warming
13. additionExcess Et3N was then added to the solution
14. customto precipitate the product as the free base which
15. filtrationwas then filtered
16. washwashed with water
17. customdried under reduced pressure