反应详情

N-(6-Nitroquinolin-4-yl)-N-(N,N-dimethylaminoethyl)-2-iodo-5,6-dimethoxybenzamide (8c). Oxalyl chloride (1.5 g, 12.0 mmol) was added to a solution of 3,4-dimethoxy-6-iodobenzoic acid (985 mg, 3.2 mmol) in anhydrous methylene chloride (20 mL), and the stirred mixture was refluxed for 3 hours. The mixture was then concentrated to dryness under reduced pressure. The acid chloride was redissolved in 20 mL of anhydrous methylene chloride, and this solution was added to a solution of 7c (700 mg, 2.7 mmol) and triethylamine (2.0 g, 20.0 mmol) in methylene chloride (30 mL), and the resulting mixture was stirred at reflux for 2 hours. The reaction mix was cooled and washed with saturated sodium bicarbonate (3×75 mL), and extracted with 5% aqueous HCl (4×100 mL). The combined aqueous extracts were basified with 30% NaOH and then extracted with chloroform (3×100 mL). Combined organic extracts were then dried (MgSO4) and evaporated to give 1.15 g of the amide, in 78% yield; 1H NMR (CDCl3) δ 2.23 (s, 6H), 2.63 (m, 2H), 3.35 (s, 3H), 3.71 (s, 3H), 3.96 (m, 1H), 4.29 (m, 1H), 6.50 (s, 1H), 6.94 (s, 1H), 7.79 (d, 1H, J=5.2), 8.22 (d, 1H, J=9.2), 8.48 (d, 1H, J=9.2), 9.0 (d, 1H, J=5.2), 9.28 (s, 1H); 13C NMR (CDCl3) δ 45.5, 48.0, 55.6, 56.1, 56.8, 82.3, 110.7, 120.9, 121.5, 122.9, 123.4, 125.5, 132.2, 133.7, 145.9, 148.4, 149.1, 149.8, 151.5, 154.1, 169.7; IR (CHCl3) 1345, 1535, 1655.

1. temperaturethe stirred mixture was refluxed for 3 hours
2. concentrationThe mixture was then concentrated to dryness under reduced pressure
3. dissolutionThe acid chloride was redissolved in 20 mL of anhydrous methylene chloride
4. temperatureat reflux for 2 hours
5. additionThe reaction mix
6. temperaturewas cooled
7. washwashed with saturated sodium bicarbonate (3×75 mL)
8. extractionextracted with 5% aqueous HCl (4×100 mL)
9. extractionextracted with chloroform (3×100 mL)
10. dry with materialCombined organic extracts were then dried (MgSO4)
11. customevaporated