Phthalic Anhydride → 2-(2-(2-Oxoindolin-3-yl)ethyl)isoindoline-1,3-dione

HRID 1749527노트

반응식

HRID 1749527 반응식
Cl.[NH2:2][CH2:3][CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:14].[C:15]1(=O)[O:20][C:18](=[O:19])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12>C1(C)C=CC=CC=1.CN1C(=O)CCC1>[O:14]=[C:6]1[CH:5]([CH2:4][CH2:3][N:2]2[C:18](=[O:19])[C:17]3[C:16](=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:15]2=[O:20])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7]1

참가 물질

4

반응물 2

HCID 6811Phthalic AnhydrideHCID 117012923-(2-aminoethyl)-2,3-dihydro-1H-indol-2-one hydrochloride

생성물 1

HCID 1181621082-(2-(2-Oxoindolin-3-yl)ethyl)isoindoline-1,3-dione수율 56.4%

시약·촉매·용매 1

HCID 21877177toluene N-methylpyrrolidone용매

실험 절차

A mixture of 3-(2-aminoethyl)indolin-2-one hydrochloride (3.20 g, 15.06 mmol), phthalic anhydride (3.34 g, 22.59 mmol) and TEA (4.56 g, 45.18 mmol) in toluene/NMP (20 mL/10 mL). The mixture was heated under reflux for 3 h. The reaction mixture was concentrated and the resulting mixture was washed with saturated aqueous ammonium chloride and brine. The separated organic layer was dried over anhydrous sodium sulfate and filtered. Concentration under vacuum gave the crude product, which was purified by silica gel column chromatography (30% ethyl acetate in petroleum ether) to afford the title compound (2.60 g, 8.50 mmol, 56% yield) as a brown solid. MS (ESI) m/z 307.2 [M+H]+.

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 h
  3. concentrationThe reaction mixture was concentrated
  4. washthe resulting mixture was washed with saturated aqueous ammonium chloride and brine
  5. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationConcentration under vacuum
  8. customgave the crude product, which
  9. customwas purified by silica gel column chromatography (30% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-461153b79e1e45dba12ce8d99d44aadf
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156798B2

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