Formic Acid → 6-Bromo-4,4-dimethyl-3,4-dihydroquinoline-1(2H)-carbaldehyde

HRID 24127

Reaktionsgleichung

Reaktionsgleichung von HRID 24127
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6][C:5]2([CH3:13])[CH3:12].[CH:14](O)=[O:15]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:14]=[O:15])[CH2:7][CH2:6][C:5]2([CH3:13])[CH3:12]

Komponenten

3

Edukt 2

HCID 284Formic AcidHCID 108239326-Bromo-1,2,3,4-tetrahydro-4,4-dimethylquinoline

Produkt 1

HCID 225688836-Bromo-4,4-dimethyl-3,4-dihydroquinoline-1(2H)-carbaldehydeAusbeute 90 %

Versuchsvorschrift

A solution of 6-bromo-4,4-dimethyl-1,2,3,4-tetrahydroquinoline, available in accordance with U.S. Pat. No. 5,089,509, the specification of which is incorporated herein by reference (1.8 g, 7.5 mmol) in 10 mL of formic acid was refluxed for 3 h. The reaction mixture was then cooled to ambient temperature and poured into ice-cold saturated aqueous sodium bicarbonate solution and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a residue which was subjected to flash column chromatography over silica gel (230-400 mesh) using 15-25% ethyl acetate in hexane as the eluent to afford the title compound as a pale yellow solid (1.8 g, 90%).

Aufarbeitung

  1. temperaturewas refluxed for 3 h
  2. additionpoured into ice-cold saturated aqueous sodium bicarbonate solution
  3. extractionextracted with diethyl ether (×2)
  4. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to a residue which

Quellen und Nachweise

ORD-Eintrag
ord-9e01a64247cb4cbd93719c5bfbb13e61
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855512B2

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