Ammonium Hydroxide → 3-(p-Chlorophenyl)-2-[2-(diethylamino)ethyl]isoindole-1-carboxylic acid ethyl ester hydrochloride

HRID 1679069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1679069
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].[CH2:9]([O:11][C:12](=[O:30])[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21](=O)[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)=O)[CH3:10].[OH-].[NH4+]>C(O)=O>[ClH:28].[CH2:9]([O:11][C:12]([C:13]1[N:6]([CH2:5][CH2:4][N:3]([CH2:7][CH3:8])[CH2:1][CH3:2])[C:21]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:16]2[C:15]=1[CH:20]=[CH:19][CH:18]=[CH:17]2)=[O:30])[CH3:10]

Komponenten

5

Edukt 3

HCID 14923Ammonium HydroxideHCID 60993N,N-DiethylethylenediamineHCID 53699063HCID 53699063, Verbindung

Produkt 1

HCID 706202883-(p-Chlorophenyl)-2-[2-(diethylamino)ethyl]isoindole-1-carboxylic acid ethyl ester hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

A mixture of 0.83 g. of formic acid and 1.05 g. of 2-diethylaminoethylamine is treated at room temperature with 0.95 g. of [o-(p-chlorobenzoyl)phenyl]-glyoxylic acid ethyl ester and subsequently stirred at 140° C. for 2 hours. After cooling, the obtained solution is made alkaline with 2-N ammonium hydroxide with addition of ice and extracted with ether. The extract, shielded from daylight, is washed with water, dried over sodium sulfate, concentrated and chromatographed on 70 g. of silica gel with ether as the eluant. The homogeneous fractions are combined, concentrated to a volume of 15-20 ml. and treated with ethereal hydrochloric acid. The crystallized hydrochloride is removed by filtration and washed with ether, and there is obtained 3-(p-chlorophenyl)-2-[2-(diethylamino)ethyl]isoindole-1-carboxylic acid ethyl ester hydrochloride; melting point 202°-204° C. (decomposition). Recrystallization from methylene chloride/ether does not increase the melting point.

Aufarbeitung

  1. additionA mixture of 0.83 g
  2. temperatureAfter cooling
  3. additionwith addition of ice
  4. extractionextracted with ether
  5. washis washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customchromatographed on 70 g
  9. concentrationconcentrated to a volume of 15-20 ml
  10. additionand treated with ethereal hydrochloric acid
  11. customThe crystallized hydrochloride is removed by filtration
  12. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-314a990192da44eebc82279f778628a0
Quelldatensatz
uspto-grants-1978_03
Patentnummer
US04077978

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