反应详情

Sodium hydroxide solution (1.5M, 50 ml) was added dropwise to an ice cooled mixture of bromoacetyl bromide (11 g) and methyl N-methylanthranilate (8.2 g) in dichloromethane (250 ml). After the addition was complete (15 min) stirring was continued at room temperature for 20 min. The organic phase was then separated, washed with 1N HCl (50 ml), brine (50 ml), NaHCO3 solution (50 ml), dried (MgSO4) and evaporated to give a colourless oil which crystallised on standing. Trituration with pet-ether (bp 60°-80°) followed by filtration afforded 10.4 g of product as a colourless solid. 1H NMR (360 MHz, CDCl3) δ: 3.23 (3H, s), 3.54 and 3.60 (2H, ABq J=11 Hz), 3.90 (3H, s), 7.40 (1H, d, J=8 Hz), 7.51 (1H, t, J=8 Hz), 7.65 (1H, t, J=8 Hz), 8.04 (1H, d, J=8 Hz).

1. temperaturecooled
2. additionAfter the addition
3. custom(15 min)
4. customThe organic phase was then separated
5. washwashed with 1N HCl (50 ml), brine (50 ml), NaHCO3 solution (50 ml)
6. dry with materialdried (MgSO4)
7. customevaporated
8. customto give a colourless oil which
9. customcrystallised
10. filtrationTrituration with pet-ether (bp 60°-80°) followed by filtration