Benzaldehyde → 8-(Phenylmethylidene)-5,6,7,8-tetrahydroquinoline

HRID 252079

Reaktionsgleichung

Reaktionsgleichung von HRID 252079
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(OC(=O)C)(=O)C.[OH-].[Na+]>>[CH:11](=[C:9]1[C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6][CH2:7][CH2:8]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 4

HCID 240BenzaldehydeHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 663355,6,7,8-Tetrahydroquinoline

Produkt 1

HCID 540746508-(Phenylmethylidene)-5,6,7,8-tetrahydroquinoline

Versuchsvorschrift

A solution of 5,6,7,8-tetrahydroquinoline (18.2 g, 137 mmol), benzaldehyde (17.7 g, 166. mmol), and acetic anhydride (24.5 mL, 254 mmol) was heated at 165° C. for 16 h. The reaction mixture was cooled to room temperature (rt). Crushed ice was added, and the mixture was slowly basified with NaOH (solid and 2 M NaOH) to pH ˜7. The aqueous layer was extracted with hexane/ethyl acetate (1:1 solution) 3 times. The pooled organic layers were dried over magnesium sulfate. The mixture was filtered, and the solvents were removed under vacuum to give 8-benzylidene-5,6,7,8-tetrahydro-quinoline (2) as a brown solid.

Aufarbeitung

  1. additionCrushed ice was added
  2. extractionThe aqueous layer was extracted with hexane/ethyl acetate (1:1 solution) 3 times
  3. dry with materialThe pooled organic layers were dried over magnesium sulfate
  4. filtrationThe mixture was filtered
  5. customthe solvents were removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c0e0a7d97e6e44e2b245718b4b9a74a5
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868020B2

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