Hydrochloric Acid → 1-(Quinolin-6-yl)cyclopropan-1-amine

HRID 876793

Reaktionsgleichung

Reaktionsgleichung von HRID 876793
[CH2:1]([Mg]Br)[CH3:2].[N:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]#[N:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.B(F)(F)F.CCOCC.Cl.[OH-].[Na+]>CCOCC>[N:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]3([NH2:16])[CH2:2][CH2:1]3)=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 592995Quinoline-6-carbonitrileHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 630972281-(Quinolin-6-yl)cyclopropan-1-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

Ethylmagnesium bromide (7.7 mmol, 3 M in ethyl ether) was added to a solution of quinoline-6-carbonitrile (0-4) (540 mg, 3.5 mmol) and Ti(Oi-Pr)4 (3.9 mmol, 1.16 mL) in Et2O (15 mL) at −70° C. The resulting yellow solution was stirred for 10 mins, warmed to room temperature over 1.5 h, and then was treated with BF3.OEt2 (7 mmol, 0.88 mL). The resulting mixture was stirred for 1 h. Then 1N aqueous HCl (11 mL) and ethyl ether (40 mL) were added, followed by NaOH (10% aq, 30 mL). The mixture was extracted with ethyl ether. The combined ethyl ether layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford the crude title compound, which was used for the next step without further purification. MS (m/z): 185 (M+1)+.

Aufarbeitung

  1. stirringThe resulting mixture was stirred for 1 h
  2. extractionThe mixture was extracted with ethyl ether
  3. dry with materialThe combined ethyl ether layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b44d7f2fca014da9aa91f74bc59e9afa
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987269B2

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