반응 #42471

반응 방정식

Methyl 3-bromo-5-(butylamino)-4-hydroxybenzoate

sodium bicarbonate

isobutyl methyl ketone water

chloroacetyl chloride

→

Methyl 8-bromo-4-butyl-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

용매

chloroform

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도at reflux for 14 h
3. 3
   온도The mixture was cooled to room temperature
4. 4
   기타the layer separated
5. 5
   세척The organic layer was washed with water, and brine
6. 6
   건조dried (magnesium sulfate)
7. 7
   여과filtered
8. 8
   농축concentrated under reduced pressure
9. 9
   기타to give a white solid
10. 10
    기타1H NMR (300 MHz, CDCl3) δ 7.94, 7.62, 4.76, 3.98, 3.93, 1.65, 1.43, 0.97, which was used in the next step without further purification or characterization

실험 절차

To an ice-cold, stirred solution of Methyl 3-bromo-5-(butylamino)-4-hydroxybenzoate (440 mg) and sodium bicarbonate (280 mg) in 1:1 isobutyl methyl ketone/water (10 mL) was added chloroacetyl chloride (226 mg). The mixture was stirred for 1 h, warmed to room temperature, and heated at reflux for 14 h. The mixture was cooled to room temperature, diluted with chloroform, and the layer separated. The organic layer was washed with water, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure to give a white solid: 1H NMR (300 MHz, CDCl3) δ 7.94, 7.62, 4.76, 3.98, 3.93, 1.65, 1.43, 0.97, which was used in the next step without further purification or characterization.

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