N-Boc-4-hydroxyaniline → HCID 42625417, Verbindung

HRID 1864671

Reaktionsgleichung

Reaktionsgleichung von HRID 1864671
[C:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC(C)([O-])C.[K+].Cl[C:23]1[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH3:30])[C:24]=1[N+:31]([O-:33])=[O:32]>CN(C=O)C>[CH3:30][NH:29][C:25]1[C:24]([N+:31]([O-:33])=[O:32])=[C:23]([O:15][C:12]2[CH:11]=[CH:10][C:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[CH:14][CH:13]=2)[CH:28]=[CH:27][N:26]=1

Komponenten

5

Edukt 3

HCID 2756771N-Boc-4-hydroxyanilineHCID 23665647Potassium tert-butoxideHCID 249031234-Chloro-N-methyl-3-nitropyridin-2-amine

Produkt 1

HCID 42625417HCID 42625417, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

N-Boc-4-hydroxyaniline (334 mg, 1.6 mmol) was dissolved in dry DMF (5 mL) and the solution was degassed by argon bubbling for 10 minutes. Potassium tert-butoxide (179 mg, 1.6 mmol) was added, and the stirring and argon bubbling continued for 50 minutes. 4-Chloro-N-methyl-3-nitropyridin-2-amine (260 mg, 1.4 mmol) was added to the reaction mixture. The reaction mixture was heated and stirred at 80° C. for 9 hours, under argon. The solvent was evaporated and the residue was extracted between DCM and aqueous NaOH 1M. The extraction was repeated twice, the organic layer was dried over MgSO4, and evaporated. The residue was purified by column chromatography (eluent gradient DCM to DCM:AcOEt 15:1) to afford the title compound (300 mg, 60%). 1H-NMR (δ, ppm, DMSO-d6): 1.48 (s, 9H, t-Bu), 2.91 (d, 3H, Me, J=4.60 Hz), 5.94 (d, 1H, HPy,5, J=5.70 Hz), 7.09 (d, 2H, Harom,Ph,3+5, J=9.00 Hz), 7.45 (m, 1H, NHPy), 7.53 (d, 2H, Harom,Ph,2+6), 8.07 (d, 1H, HPy,6), 9.46 (s, 1H, NH).

Aufarbeitung

  1. customthe solution was degassed by argon bubbling for 10 minutes
  2. temperatureThe reaction mixture was heated
  3. customThe solvent was evaporated
  4. extractionthe residue was extracted between DCM and aqueous NaOH 1M
  5. extractionThe extraction
  6. dry with materialthe organic layer was dried over MgSO4
  7. customevaporated
  8. customThe residue was purified by column chromatography (eluent gradient DCM to DCM:AcOEt 15:1)

Quellen und Nachweise

ORD-Eintrag
ord-4e3e0c42a6fb4c2e8dc509ade7274c1c
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625922B2

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