Triphenylphosphine → 3-Nitro-6-(2-(pyrrolidin-1-yl)ethoxy)quinoline

HRID 1512113

Reaktionsgleichung

Reaktionsgleichung von HRID 1512113
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[CH:5]2.[N:15]1([CH2:20][CH2:21]O)[CH2:19][CH2:18][CH2:17][CH2:16]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[N+:12]([C:6]1[CH:7]=[N:8][C:9]2[C:4]([CH:5]=1)=[CH:3][C:2]([O:1][CH2:21][CH2:20][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[CH:11][CH:10]=2)([O-:14])=[O:13]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 762881-PyrrolidineethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 595075803-Nitroquinolin-6-ol

Produkt 1

HCID 595075993-Nitro-6-(2-(pyrrolidin-1-yl)ethoxy)quinolineAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6-Hydroxy-3-nitroquinoline (148 mg, 0.78 mmol) was dissolved in THF (18 mL). 2-(Pyrrolidin-1-yl)ethanol (0.091 mL, 0.78 mmol) and triphenylphosphine (306 mg, 1.17 mmol) were added. Lastly, diethyl azodicarboxylate (0.184 mL, 1.17 mmol) was added and the reaction mixture was allowed to stir at room temperature for 2 hours. The solvent was then concentrated in vacuo and the residue was purified by flash chromatography (SiO2) to yield 134 mg (60%) of 3-nitro-6-(2-(pyrrolidin-1-yl)ethoxy)quinoline. LC/MS (m/z): 288.1 (MH+), Rt 1.80 minutes.

Aufarbeitung

  1. concentrationThe solvent was then concentrated in vacuo
  2. customthe residue was purified by flash chromatography (SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-5f1d320b05c54b64b95ff23789ad63df
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217035B2

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