Dichloromethane → 5-Bromo-1-(2-nitrophenyl)-2,3-dihydro-1H-indole

HRID 4022

반응식

HRID 4022 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.N1C(C)=CC(C)=CC=1C.F[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28].ClCCl>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28])[CH2:6][CH2:5]2

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 79532,4,6-TrimethylpyridineHCID 738951-Fluoro-2-nitrobenzeneHCID 34115665-Bromoindoline

생성물 1

HCID 138233325-Bromo-1-(2-nitrophenyl)-2,3-dihydro-1H-indole수율 55%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

5-Bromoindoline (4.0 g, 0.02 mole), collidine (3.6 g, 0.03 mole), and o-fluoronitrobenzene (2.8 g, 0.02 mole) in xylene (25 ml) were heated at 185° C. (oil bath temperature) for 24 hours. The mixture was cooled to room temperature and poured into dichloromethane. The dichloromethane solution was washed with 1N hydrochloric acid (3 times, 150 ml), brine (200 ml), dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated. Crystallization of the residue was induced by stirring in ether (15 ml) followed by hexane (200 ml), then chilling in the refrigerator overnight. The solid was filtered and washed with hexane and dried to yield 3.5 g (55%) of product. Recrystallization from 2-propanol yielded the analytical sample, mp 12°-114° C.

후처리

  1. washThe dichloromethane solution was washed with 1N hydrochloric acid (3 times, 150 ml), brine (200 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was evaporated
  5. customCrystallization of the residue
  6. temperaturechilling in the refrigerator overnight
  7. filtrationThe solid was filtered
  8. washwashed with hexane
  9. customdried

출처 및 근거

ORD 기록
ord-5d5026eae7df4acdbb2617c4f3ddf508
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04723007

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