Phenol → 1,3-dihydro-1-(propyl-4-pyridinylamino)-2H-indol-2-one

HRID 128678노트

반응식

HRID 128678 반응식
[CH2:1]([NH:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][C:6]1=[O:14])[CH2:2][CH3:3].C1(O)C=CC=CC=1.Cl.Br[C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1.[OH-].[Na+]>>[CH2:1]([N:4]([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)[N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][C:6]1=[O:14])[CH2:2][CH3:3]

참가 물질

5

반응물 4

HCID 996PhenolHCID 14798Sodium HydroxideHCID 881004-Bromopyridinium chlorideHCID 157036281-(Propylamino)-oxindole

생성물 1

HCID 149942611,3-dihydro-1-(propyl-4-pyridinylamino)-2H-indol-2-one수율 14.4%

실험 절차

To a stirred solution of 1,3-dihydro-1-(propylamino)-2H-indol-2-one (10.4 g) and phenol (30.8 g), preheated to 150° C. under nitrogen, was added 4-bromopyridine hydrochloride (11.04 g) over 5 min. Heating was continued for 7 hours at which time the reaction mixture was cooled to room temperature and made basic by slow addition of dilute aqueous sodium hydroxide. The product was extracted four times with ethyl acetate and the combined organic layers back-extracted with dilute aqueous sodium hydroxide, washed with brine, and dried (K2CO3). Filtration and concentration gave the crude product. Purification via flash column chromatography (silica gel, EtOAc), preparative high performance liquid chromatography (HPLC) (silica gel, EtOAc→2% Et3N/0-7% MeOH/EtOAc), and a third column (alumina, EtOAc) followed. Recrystallization from ethyl acetate-pentane afforded 2.10 g (14%) of 1,3-dihydro-1-(propyl-4-pyridinylamino)-2H-indol-2-one, as a solid, m.p. 140°-143° C.

후처리

  1. custompreheated to 150° C. under nitrogen
  2. temperatureHeating
  3. extractionThe product was extracted four times with ethyl acetate
  4. extractionthe combined organic layers back-extracted with dilute aqueous sodium hydroxide
  5. washwashed with brine
  6. dry with materialdried (K2CO3)
  7. filtrationFiltration and concentration
  8. customgave the crude product
  9. customPurification via flash column chromatography (silica gel, EtOAc), preparative high performance liquid chromatography (HPLC) (silica gel, EtOAc→2% Et3N/0-7% MeOH/EtOAc)
  10. customRecrystallization from ethyl acetate-pentane

출처 및 근거

ORD 기록
ord-07e7d2e26f004c92b8dad06c8a4eb72b
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464846

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