반응 #45566

반응 방정식

dioxane

6-fluoro-7-methoxy-4-methyl-1H-indole-2,3-dione

hydrogen peroxide

sodium hydroxide

→

2-Amino-4-fluoro-3-methoxy-6-methylbenzoic acid

용매

water

water

반응 조건

후처리

1. 1
   온도With cooling with ice
2. 2
   기타The reaction liquid
3. 3
   세척was washed twice with chloroform, acetic acid
4. 4
   workup.ADDITIONwas added to the aqueous layer
5. 5
   추출by controlling at pH of 3 to 4 and extraction three times with ethyl acetate
6. 6
   세척the organic layer was washed twice with saturated brine
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   여과After filtration and concentration under reduced pressure
9. 9
   농축the eluate with chloroform alone was concentrated under reduced pressure
10. 10
    기타to obtain the entitled compound (1.54 g, 28% from I-30) as a yellow solid

실험 절차

With cooling with ice, a solution of 30% aqueous hydrogen peroxide (6.3 ml, 61.5 mmol) diluted with water (8.2 ml) was added to a dioxane (50 ml) solution of 6-fluoro-7-methoxy-4-methyl-1H-indole-2,3-dione (I-28) (2.57 g), at the same temperature, a water (230 ml) solution of sodium hydroxide (6.15 g, 153.8 mmol) was dropwise added, taking 1 hour, followed by stirring for 4 hours with gradually heating up to room temperature. The reaction liquid was washed twice with chloroform, acetic acid was added to the aqueous layer followed by controlling at pH of 3 to 4 and extraction three times with ethyl acetate, the organic layer was washed twice with saturated brine, then dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with chloroform alone was concentrated under reduced pressure to obtain the entitled compound (1.54 g, 28% from I-30) as a yellow solid.

출처