Sodium Hydroxide → N-(m-nitrocinnamyl)-isoindoline hydrochloride

HRID 1764111Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1764111
Cl.[CH2:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][NH:3]1.[OH-].[Na+].[N+:13]([C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=1)[CH:19]=[CH:20][CH2:21][Cl:22])([O-:15])=[O:14]>O.C(O)C>[ClH:22].[N+:13]([C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=1)[CH:19]=[CH:20][CH2:21][N:3]1[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:2]1)([O-:15])=[O:14]

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 43777491-(3-Chloro-propenyl)-3-nitro-benzeneHCID 123110312,3-dihydro-1H-isoindole hydrochloride

Produkt 1

HCID 70616192N-(m-nitrocinnamyl)-isoindoline hydrochlorideAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

The process for the preparation of this compound and its physical properties will be given below. A solution of 5.68 grams of isoindoline hydrochloride and 2.86 grams of sodium hydroxide in 15 milliliters of water is added to a solution of 6.8 grams of m-nitrocinnamyl chloride in 160 milliliters of ethanol, and the mixture is stirred for 10 hours at room temperature. After completion of the reaction, the reaction product is concentrated, and the residue is extracted with chloroform. The extract is then purified by silica gel column chromatography, following which the resulting oily product is converted to a hydrochloride in a customary manner and recrystallized from ethanol to obtain 5.6 grams (yield 52%) of N-(m-nitrocinnamyl)-isoindoline hydrochloride as crystals having a melting point of 208°-210° C. (decomposition).

Aufarbeitung

  1. customThe process for the preparation of this compound and its physical properties
  2. customAfter completion of the reaction
  3. concentrationthe reaction product is concentrated
  4. extractionthe residue is extracted with chloroform
  5. customThe extract is then purified by silica gel column chromatography
  6. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-0cb01a295cd8484ba4fc4671b7de70c3
Quelldatensatz
uspto-grants-1978_09
Patentnummer
US04115398

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