反応 #331992

反応方程式

p-Toluenesulfonyl chloride

3-Chloroperoxybenzoic acid

7-Bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinoline

Ammonium hydroxide

→

7-bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine

溶媒

chloroform

反応条件

後処理

1. 1
   workup.STIRRINGAfter stirring for 16 hours
2. 2
   その他the layers were separated
3. 3
   抽出the aqueous fraction was extracted with chloroform
4. 4
   洗浄The combined organic fractions were sequentially washed with 5% aqueous sodium bicarbonate, water and brine
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   ろ過filtered
7. 7
   濃縮concentrated under reduced pressure
8. 8
   その他The residue was purified by flash column chromatography on silica gel
9. 9
   その他The purification
10. 10
    洗浄was carried out eluting with chloroform
11. 11
    その他The material recovered from the column
12. 12
    その他was recrystallized from acetonitrile

実験手順

7-Bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinoline (20 g) was dissolved in chloroform (400 mL). 3-Chloroperoxybenzoic acid (60% pure, 17.1 g) was added in 2 g portions over a 5 minute period and the reaction was stirred for 1 hour. Ammonium hydroxide (300 mL) was added and the mixture was cooled to 5° C. with an ice/water bath. p-Toluenesulfonyl chloride (9.4 g) was added at the rate of 1 g/min to minimize gas evolution. After stirring for 16 hours, the layers were separated and the aqueous fraction was extracted with chloroform. The combined organic fractions were sequentially washed with 5% aqueous sodium bicarbonate, water and brine; dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel. The polar component of the eluent was chloroform:methanol:ammonium hydroxide 80:18:2 (CMA). The purification was carried out eluting with chloroform:CMA in a gradient from 98:2 to 88:12. The material recovered from the column was recrystallized from acetonitrile to yield 7.0 g of 7-bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine as a tan granular powder.

出典