Toluene → 2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine

HRID 2253354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2253354
C([NH:8][C:9]1[C:10]([CH3:29])=[C:11]([CH3:28])[C:12]2[O:16][C:15]([CH3:18])([CH3:17])[CH:14]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[C:13]=2[C:26]=1[CH3:27])C1C=CC=CC=1.C1(C)C=CC=CC=1.C(O)(C)C>[Pd].[C].O>[CH3:17][C:15]1([CH3:18])[CH:14]([C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)[C:13]2[C:26]([CH3:27])=[C:9]([NH2:8])[C:10]([CH3:29])=[C:11]([CH3:28])[C:12]=2[O:16]1

Komponenten

6

Edukt 3

HCID 1140TolueneHCID 3776IsopropanolHCID 10271436HCID 10271436, Verbindung

Produkt 1

HCID 106853092,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amineAusbeute 88,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a mixture of N-benzyl-2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine (80 g), toluene (240 mL) and isopropanol (80 mL) was added 10% Pd-carbon (a product containing 50% water, 4 g), and the mixture was hydrogenated at 35° C. under atmospheric pressure. After completion of the reaction, the catalyst was filtered. Concentrated hydrochloric acid (19.2 mL) was added to the filtrate and the mixture was stirred at 10° C. or below for 1 hour. Precipitated crystals were filtered. The crystals were added to a mixture of methanol (560 mL) and water (80 mL) and the mixture was heated to 50° C. to dissolve the crystals. Then, 25% aqueous ammonia water was added dropwise to the solution to adjust to pH 8.5. Precipitated crystals were filtered to obtain the title compound (54.32 g, 88.6%).

Aufarbeitung

  1. customwas hydrogenated at 35° C. under atmospheric pressure
  2. customAfter completion of the reaction
  3. filtrationthe catalyst was filtered
  4. additionConcentrated hydrochloric acid (19.2 mL) was added to the filtrate
  5. customPrecipitated crystals
  6. filtrationwere filtered
  7. additionThe crystals were added to a mixture of methanol (560 mL) and water (80 mL)
  8. dissolutionto dissolve the crystals
  9. additionThen, 25% aqueous ammonia water was added dropwise to the solution
  10. customPrecipitated crystals
  11. filtrationwere filtered

Quellen und Nachweise

ORD-Eintrag
ord-316d46839f3e42caa377f8c8406edb69
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07323577B2

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