Ethylamine → 6-Ethoxy-2-(ethylamino)quinoline-3-carbaldehyde

HRID 1620209Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620209
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH2:15][CH3:16])[CH:8]=2)[N:3]=1.[CH2:17]([NH2:19])[CH3:18]>>[CH2:15]([O:14][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:19][CH2:17][CH3:18])[C:11]([CH:12]=[O:13])=[CH:10]2)[CH3:16]

Komponenten

3

Edukt 2

HCID 6341EthylamineHCID 7886582-Chloro-6-ethoxyquinoline-3-carbaldehyde

Produkt 1

HCID 866698196-Ethoxy-2-(ethylamino)quinoline-3-carbaldehydeAusbeute 101,7 %

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a stirred solution of 2-chloro-6-ethoxyquinoline-3-carbaldehyde (298 mg, 1.26 mmol) in a 20 mL microwave vial equipped with a magnetic stirrer was added ethylamine (2.0 N in THF, 13.0 mL, 26.0 mmol) and the reaction mixture was stirred for 10 h at 140° C. under microwave irradiation then for 13 h at 130° C. still under microwave irradiation. After cooling to RT, the reaction mixture was concentrated to dryness at 40° C. under vacuum and the resulting yellow oil was taken up in a mixture of THF:1 N aq. HCl=1:1 (50 mL) and stirred for 1 h at RT. The volatiles were then removed at 40° C. under vacuum and the residue was then neutralised with saturated NaHCO3 aqueous solution before extraction with CH2Cl2 (100 mL). The organic phase was washed with brine (20 mL), dried over MgSO4, filtered, and concentrated under vacuum, which gave 6-ethoxy-2-(ethylamino)quinoline-3-carbaldehyde SLA 41034 as an orange solid (313 mg, >100% yield).

Aufarbeitung

  1. customfor 13 h at 130° C. still under microwave irradiation
  2. temperatureAfter cooling to RT
  3. concentrationthe reaction mixture was concentrated to dryness at 40° C. under vacuum
  4. additionthe resulting yellow oil was taken up in a mixture of THF
  5. stirring1 N aq. HCl=1:1 (50 mL) and stirred for 1 h at RT
  6. customThe volatiles were then removed at 40° C. under vacuum
  7. extractionthe residue was then neutralised with saturated NaHCO3 aqueous solution before extraction with CH2Cl2 (100 mL)
  8. washThe organic phase was washed with brine (20 mL)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum, which

Quellen und Nachweise

ORD-Eintrag
ord-f095a5f0830a46b29ea71986054c092d
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772316B2

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