1,2-Dimethoxyethane → 3-(1-Isopropyl-7-methyl-1,2,3,4-tetrahydro-6-quinolinyl)-4-methoxybenzaldehyde

HRID 1884496Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1884496
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[N:8]([CH:13]([CH3:15])[CH3:14])[CH2:7][CH2:6][CH2:5]2.[C:16](=[O:19])([O-])[O-].[K+].[K+].CO[CH2:24][CH2:25][O:26][CH3:27]>O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:13]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([C:3]3[CH:2]=[C:11]([CH:10]=[CH:24][C:25]=3[O:26][CH3:27])[CH:16]=[O:19])=[C:11]([CH3:12])[CH:10]=2)[CH2:5][CH2:6][CH2:7]1)([CH3:15])[CH3:14]

Komponenten

7

Edukt 3

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 222683656-Bromo-1-isopropyl-7-methyl-1,2,3,4-tetrahydro-quinoline

Produkt 1

HCID 222682923-(1-Isopropyl-7-methyl-1,2,3,4-tetrahydro-6-quinolinyl)-4-methoxybenzaldehydeAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 6-bromo-1-isopropyl-7-methyl-1,2,3,4-tetrahydro-quinoline (0.85 g, 3.16 mmol), 2-methoxy-5-formyl boronic acid (1.13 g, 6.31 mmol) and potassium carbonate (1.70 g, 12.64 mmol) in 1,2-dimethoxyethane (30 mL) and water (1.5 mL) was degassed with argon for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.80 g, 0.63 mmol) was added and the mixture heated at reflux under argon for 35 hours. The solution was cooled to room temperature, diluted with ethyl acetate and washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was chromatographed and silica gel (eluent: ethyl acetate/hexane, 1:9) to give 0.81 g of 3-(1-isopropyl-7-methyl-1,2,3,4-tetrahydro-6-quinolinyl)-4-methoxybenzaldehyde (79%). 1H NMR (500 MHz; CDCl3): δ1.18 (s, 3 H); 1.20 (s, 3 H); 1.94 (m, 2 H); 2.06 (s, 3 H); 2.72 (m, 2 H); 3.18 (m, 2 H); 3.85 (s, 3 H); 4.16 (m, 1 H); 6.57 (s, 1 H); 6.78 (s, 1 H); 7.02 (d, 1 H); 7.69 (d, 1 H); 7.34 (s, 1 H); 7.84 (m, 1 H); 9.89 (s, 1 H).

Aufarbeitung

  1. customwas degassed with argon for 15 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux under argon for 35 hours
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-f9c92c14a4ec4c4b8fa5f20523e59a26
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06765013B2

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