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

HRID 1749527ノート

反応式

HRID 1749527 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21877177toluene N-methylpyrrolidone溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-461153b79e1e45dba12ce8d99d44aadf
出典データセット
uspto-grants-2015_10
特許番号
US09156798B2

反応ノート

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