Water → 2,3-Dihydro-1H-indene-1,3-diamine

HRID 264347Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 264347
[C:1]1(=[N:12]O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[N:10]O)[CH2:2]1.[Na].O>C(O)C>[NH2:10][CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:1]([NH2:12])[CH2:2]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 5360545Sodium2×HCID 135494888HCID 135494888, Verbindung

Produkt 1

HCID 190367312,3-Dihydro-1H-indene-1,3-diamineAusbeute 69,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 20 g of a 1,3-indandione dioxime in 2 L of absolute ethanol was cautiously added 160 g of sodium in portions during 1 hr (at such a rate to maintain reflux). After disappearance of the sodium, 300 mL of water was slowly added and the solution concentrated in vacuo to remove most of the ethanol. The resulting solution was acidified with conc. hydrochloric acid to pH 1-2 followed by extraction with methylene chloride to recover unreacted started material. The aqueous layer was basified with 10% sodium hydroxide to pH 12 and extracted with methylene chloride which gave 11.7 grams of crude 1,3-diaminoindan upon solvent removal in vacuo. Purification of this material by flash column chromatography eluting with 95% ethanol/ammonium hydroxide (400:16) gave 8.75 g of the title compound as an approximately 60/40 mixture of cis to trans isomers.

Aufarbeitung

  1. customduring 1 hr
  2. temperatureto maintain
  3. temperaturereflux)
  4. concentrationthe solution concentrated in vacuo
  5. customto remove most of the ethanol
  6. extractionfollowed by extraction with methylene chloride
  7. customto recover unreacted
  8. extractionextracted with methylene chloride which

Quellen und Nachweise

ORD-Eintrag
ord-fb42257ab6bf4776862ece955c04765c
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646188

Notizen zur Reaktion

Wird geladen…