Dimethylformamide → 91374-26-4

HRID 280271

Reaktionsgleichung

Reaktionsgleichung von HRID 280271
Br.[NH2:2][CH2:3][CH2:4][C:5]1[CH:13]=[CH:12][C:11](O)=[C:10]2[C:6]=1[CH2:7][C:8](=[O:15])[NH:9]2.CN(C)C=O.[Cl:21]C1N(C2C=CC=CC=2)N=NN=1.C(=O)([O-])[O-].[K+].[K+]>O>[ClH:21].[NH2:2][CH2:3][CH2:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH2:7][C:8](=[O:15])[NH:9]2

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 12807552HCID 12807552, Verbindung

Produkt 1

HCID 2332203691374-26-4

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2.73 g (10.0 mmoles) of 4-(2-aminoethyl)-7-hydroxy-2(3H)-indolone hydrobromide, 200 cc of dimethylformamide, 1.86 g (10.3 mmoles) of 5-chloro-1-phenyl-1H-tetrazole, 10 cc of water and 2.9 g (21 mmoles) of anhydrous potassium carbonate is stirred at room temperature for 2 days or until thin layer analysis indicates that no starting material remains. The reaction is filtered and the filtrate is acidified with dil. hydrochloric acid, concentrated in vacuo and the residue triturated with abs. ethanol. The triturate is clarified with charcoal and evaporated to dryness in vacuo. The hydrochloride salt of 4-(2-aminoethyl)-7-(1-phenyl-1H-tetrazol-5-yloxy)-2(3H)-indolone is hydrogenated directly in 200 cc of glacial acetic acid using 50% by substrate weight of 10% palladium-on-carbon at moderate pressure for 20 hours at 50°. The warm reaction mixture is filtered. The catalyst is washed thoroughly with hot acetic acid. After the filtrate is concentrated in vacuo, the residue is stripped several times from dilute hydrochloric acid and crystallized from ethanol to give 4-(2-aminoethyl)-2(3H)-indolone hydrochloride.

Aufarbeitung

  1. filtrationThe reaction is filtered
  2. concentrationconcentrated in vacuo
  3. customthe residue triturated with abs
  4. customevaporated to dryness in vacuo
  5. waitThe hydrochloride salt of 4-(2-aminoethyl)-7-(1-phenyl-1H-tetrazol-5-yloxy)-2(3H)-indolone is hydrogenated directly in 200 cc of glacial acetic acid using 50% by substrate weight of 10% palladium-on-carbon at moderate pressure for 20 hours at 50°
  6. customThe warm reaction mixture
  7. filtrationis filtered
  8. washThe catalyst is washed thoroughly with hot acetic acid
  9. concentrationAfter the filtrate is concentrated in vacuo
  10. customcrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-88d1df9715bc4856ae661afeb8dc43df
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04588740

Verknüpfte Notizen

Wird geladen…