Water → 1-[4-(4-Amino-2-methylphenoxy)pyridin-2-yl]-3-(3-diethylaminopropyl)urea

HRID 2066199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2066199
[CH2:1]([N:3]([CH2:28][CH3:29])[CH2:4][CH2:5][CH2:6][NH:7][C:8]([NH:10][C:11]1[CH:16]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:19]=2[CH3:27])[CH:14]=[CH:13][N:12]=1)=[O:9])[CH3:2].[Cl-].[NH4+].O>C(O)C.[Fe]>[NH2:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][C:15]2[CH:14]=[CH:13][N:12]=[C:11]([NH:10][C:8]([NH:7][CH2:6][CH2:5][CH2:4][N:3]([CH2:28][CH3:29])[CH2:1][CH3:2])=[O:9])[CH:16]=2)=[C:19]([CH3:27])[CH:20]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 231530731-(3-Diethylaminopropyl)-3-[4-(2-methyl-4-nitrophenoxy)pyridin-2-yl]urea

Produkt 1

HCID 231531731-[4-(4-Amino-2-methylphenoxy)pyridin-2-yl]-3-(3-diethylaminopropyl)ureaAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 1-(3-diethylaminopropyl)-3-[4-(2-methyl-4-nitrophenoxy)pyridin-2-yl]urea (794 mg) in ethanol (50 ml) were added electrolytic iron powder (442 mg), ammonium chloride (847 mg) and water (10 ml), followed by stirring at 90° C. for 1 hr. The reaction mixture was allowed to cool down to room temperature, insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. To the residue was added ethyl acetate (100 ml), washed with a saturated aqueous solution of sodium hydrogencarbonate, and dried over anhydrous sodium sulfate. The solvent was removed and the resultant residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; hexane:ethyl acetate=1:1 to 1:2, ethyl acetate, then ethyl acetate:methanol=20:1 to 10:1) to provide the titled compound (110 mg, 15%).

Aufarbeitung

  1. temperatureto cool down to room temperature
  2. custominsoluble matter was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo the residue was added ethyl acetate (100 ml)
  5. washwashed with a saturated aqueous solution of sodium hydrogencarbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed
  8. customthe resultant residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent

Quellen und Nachweise

ORD-Eintrag
ord-7da8b2f8d7de4ce2bff3073ff1de1d8a
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288538B2

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