Hydrogen Bromide → 2,2,4-Trimethyl-1,2-dihydro-6-quinolinol

HRID 35861

Reaktionsgleichung

Reaktionsgleichung von HRID 35861
C([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH3:15])([CH3:14])[CH2:8][CH:7]2[CH3:16])C.Br.[OH-].[Na+].Cl.C(=O)(O)[O-].[Na+]>O>[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH3:15])([CH3:14])[CH:8]=[C:7]2[CH3:16]

Komponenten

7

Edukt 5

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 860136-Ethoxy-2,2,4-trimethyl-1,2,3,4-tetrahydroquinolineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 5997992,2,4-Trimethyl-1,2-dihydro-6-quinolinolAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

6-Ethoxy-2,2,4-trimethyl-3,4-dihydroquinoline [Ethoxyquin (70 g, 0.32 mole)], was added to 250 mL of 48% HBr, and the mixture was heated to reflux for about 1 hour. The solution was cooled and poured into water. The aqueous suspension was made basic (pH=14) by the addition of 50% aqueous NaOH. Concentrated HCl was added to adjust the pH to about 4, then the mixture was made slightly basic by the addition of saturated sodium bicarbonate solution. The mixture was extracted with EtOAc and the organic layers were dried (brine, MgSO4) and concentrated in vacuo. The thick dark oil was triturated with toluene and the insoluble residue was filtered. The crude solid was recrystallized from toluene to give the title compound as a light brown solid (mp 182°-184°, 34 g, 0.18 mole, 56%). An analytical sample was prepared by another recrystallization from toluene to provide light brown crystals, mp 182°-184°: IR (KBr) 3302, 2972, 2934, 1586, 1495, 1344, 1244, 1154, 880, 814 cm-1 ; 1H NMR (D-6 DMSO) δ 1.12 (s, 6H), 1.33 (s, 3H), 3.34 (s, 1H), 5.17 (br s, 1H), 5.26 (s, 1H), 6.28-6.42 (m, 3H); MS m/e 190 (MH+) .

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for about 1 hour
  3. temperatureThe solution was cooled
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialthe organic layers were dried (brine, MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe thick dark oil was triturated with toluene
  8. filtrationthe insoluble residue was filtered
  9. customThe crude solid was recrystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-f04a87ca74c64655ac2b84ddc4ca3c21
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05411969

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