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Acetic Acid → 2-(2-aminopropyl)-4-phenyl-1(2H)-isoquinolone

HRID 326021
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 326021
C([NH:8][CH:9]([CH3:28])[CH2:10][N:11]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:27])C1C=CC=CC=1.C(O)(=O)C.[H][H]>[C].[Pd].C(O)C>[NH2:8][CH:9]([CH3:28])[CH2:10][N:11]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:27]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 13305504HCID 13305504, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 132699402-(2-aminopropyl)-4-phenyl-1(2H)-isoquinoloneAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysator
HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

36.8 g of 2-(2-benzylaminopropyl)-4-phenyl-1(2H)-isoquinolone preapred as described above, 12 g of 5% palladium-carbon, 50 ml of glacial acetic acid and 200 ml of ethanol were mixed, and the mixture was catalytically reduced while introducing hydrogen gas into the mixture at 60° to 70° C. After completion of the reduction reaction, the mixture was filtered, and the solvent was distilled off from the filtrate. The resulting residue was dissolved in 5% hydrochloric acid and the solution was washed with ethyl acetate. The aqueous layer was separated and rendered neutral with a 10% aqueous solution of sodium hydroxide. The resulting precipitate was filtered and recrystallized from a mixture of ethyl acetate and petroleum ether to obtain 20.9 g (75% yield) of 2-(2-aminopropyl)-4-phenyl-1(2H)-isoquinolone having a melting point of 104° C. as colorless prisms.

Aufarbeitung

  1. additionwere mixed
  2. customAfter completion of the reduction reaction
  3. filtrationthe mixture was filtered
  4. distillationthe solvent was distilled off from the filtrate
  5. dissolutionThe resulting residue was dissolved in 5% hydrochloric acid
  6. washthe solution was washed with ethyl acetate
  7. customThe aqueous layer was separated
  8. filtrationThe resulting precipitate was filtered
  9. customrecrystallized from a mixture of ethyl acetate and petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-9be1b5f44fce465aa15c1c5b83fdef0e
Quelldatensatz
uspto-grants-1984_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04443607

Notizen zur Reaktion

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