반응 #62627

반응 방정식

5-chloroindoline

1,4-dichloronitrobenzene

collidine

→

product

수율 40.0%

5-Chloro-1-(4-chloro-2-nitrophenyl)indoline

수율 40.0%

용매

dimethylformamide

반응 조건

후처리

1. 1
   온도The mixture was then cooled
2. 2
   여과filtered from some insolubles
3. 3
   기타the solvent was removed in vacuo
4. 4
   온도with warming
5. 5
   기타The residue was partitioned between 1000 ml of dichloromethane and 500 ml of water
6. 6
   기타The water layer was removed
7. 7
   세척the organic phase was washed twice with 2N-hydrochloric acid, once with 2N-sodium hydroxide, once more with water
8. 8
   건조dried over Na2SO4
9. 9
   농축concentrated to an oil
10. 10
    workup.DISSOLUTIONThis was dissolved in 170 ml of methanol
11. 11
    기타at 0° C
12. 12
    기타The resultant crystals were collected
13. 13
    세척washed well with cold methanol
14. 14
    기타dried

실험 절차

A stirred solution of 123 g (0.80 mole) of 5-chloroindoline, 134 g (0.70 mole) of 1,4-dichloronitrobenzene and 97 g (0.80 mole) of collidine in 1000 ml of dimethylformamide was heated under nitrogen at 150° C. for 48 hours. The mixture was then cooled, filtered from some insolubles, and the solvent was removed in vacuo with warming. The residue was partitioned between 1000 ml of dichloromethane and 500 ml of water. The water layer was removed and the organic phase was washed twice with 2N-hydrochloric acid, once with 2N-sodium hydroxide, once more with water, dried over Na2SO4 and concentrated to an oil weighing 230 g. This was dissolved in 170 ml of methanol and stirred at room temperature and then at 0° C. The resultant crystals were collected, washed well with cold methanol, and dried. This afforded 86.5 g (40% yield) of product, m.p. 130°-133° C. 4 g of 5-chloro-1-(4-chloro-2-nitrophenyl)indoline were recrystallized from methanol in 85% yield (overall yield: 34%); m.p. 133°-135° C.

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