2,5-Dichloronitrobenzene → 5-Chloro-1-(4-chloro-2-nitrophenyl)indoline

HRID 4061

반응식

HRID 4061 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.Cl[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20].N1C(C)=CC(C)=CC=1C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20])[CH2:6][CH2:5]2

참가 물질

5

반응물 3

HCID 69772,5-DichloronitrobenzeneHCID 79532,4,6-TrimethylpyridineHCID 1175965-Chloroindoline

생성물 1

HCID 138233265-Chloro-1-(4-chloro-2-nitrophenyl)indoline수율 40%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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.

후처리

  1. temperatureThe mixture was then cooled
  2. filtrationfiltered from some insolubles
  3. customthe solvent was removed in vacuo
  4. temperaturewith warming
  5. customThe residue was partitioned between 1000 ml of dichloromethane and 500 ml of water
  6. customThe water layer was removed
  7. washthe organic phase was washed twice with 2N-hydrochloric acid, once with 2N-sodium hydroxide, once more with water
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated to an oil
  10. dissolutionThis was dissolved in 170 ml of methanol
  11. customat 0° C
  12. customThe resultant crystals were collected
  13. washwashed well with cold methanol
  14. customdried

출처 및 근거

ORD 기록
ord-8616870cff044e7d82aec6c73d00f16b
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04723003

연결된 노트

불러오는 중…