Hydroquinone → 4-(2-(Methyl(phenyl)amino)ethoxy)phenol

HRID 1053557

Reaktionsgleichung

Reaktionsgleichung von HRID 1053557
Cl[CH2:2][CH2:3][N:4]([CH3:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C([O-])([O-])=O.[K+].[K+].[C:18]1([CH:25]=[CH:24][C:22]([OH:23])=[CH:21][CH:20]=1)[OH:19]>CN(C=O)C>[CH3:11][N:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][CH2:2][O:19][C:18]1[CH:25]=[CH:24][C:22]([OH:23])=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 15476Aniline, N-(2-chloroethyl)-N-methyl-

Produkt 1

HCID 716133174-(2-(Methyl(phenyl)amino)ethoxy)phenolAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of compound 2b (500 mg, 2.95 mmol), K2CO3 (815 mg, 5.9 mmol), and KI (480 mg, 2.95 mmol) in DMF (50 mL) was bubbled with argon for 10 min Hydroquinone (649 mg, 5.9 mmol) was added to the mixture under argon. The reaction mixture was heated and stirred at 80° C. for 6 hr. After cooling to room temperature, the solvent was evaporated and the residue was quenched with 100 mL water. The mixture was adjusted pH to ˜7 with diluted hydrochloric acid. The mixture was then extracted with CH2Cl2 and the combined organic layer was washed with water and then brine and was dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography with hexane/EtOAc to provide compound 2 as a white solid (143 mg, 0.59 mmol, 20% yield). HRMS (ESI, positive) m/z calcd. for C15H18NO2 [M+H]+: 244.13321, found: 244.13323. 1H NMR (400 MHz, Chloroform-d) δ 7.29 (ddd, J=7.3, 5.6, 2.0 Hz, 2H), 6.84-6.72 (m, 7H), 4.98 (broad s, 1H), 4.11 (t, J=6.1 Hz, 2H), 3.76 (t, J=6.1 Hz, 2H), 3.08 (s, 3H).

Aufarbeitung

  1. additionwas added to the mixture under argon
  2. temperatureThe reaction mixture was heated
  3. temperatureAfter cooling to room temperature
  4. customthe solvent was evaporated
  5. customthe residue was quenched with 100 mL water
  6. extractionThe mixture was then extracted with CH2Cl2
  7. washthe combined organic layer was washed with water
  8. dry with materialbrine and was dried over Na2SO4
  9. customThe solvent was evaporated
  10. customthe residue was purified by silica gel column chromatography with hexane/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-9485e84082c149bfaa991502a46a30b8
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394233B2

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