Water → N-Methyl-4-benzyloxy-2-methylaniline

HRID 388017

Reaktionsgleichung

Reaktionsgleichung von HRID 388017
[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([CH3:16])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1(CO)C2C=CC=C[C:20]=2N=N1.[BH4-].[Na+].O>CN(C)C=O.CO.C(OCC)(=O)C>[CH3:20][NH:13][C:12]1[CH:14]=[CH:15][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][C:11]=1[CH3:16]

Komponenten

8

Edukt 4

HCID 962WaterHCID 2241691H-Benzotriazole-1-methanolHCID 4311764Sodium borohydrideHCID 167730534-(Benzyloxy)-2-methylaniline

Produkt 1

HCID 22936498N-Methyl-4-benzyloxy-2-methylanilineAusbeute 62,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

After dissolving 4-benzyloxy-2-methylaniline (6.55 g, 30.72 mmol) in N,N-dimethylformamide (10 ml) and methanol (60 ml), 1H-benzotriazole-1-methanol (4.58 g, 30.72 mmol) was added and the mixture was stirred for 30 minutes at room temperature. N,N-Dimethylformamide (20 ml) was added for complete dissolution of the precipitated crystals, sodium borohydride (2.32 g, 61.44 mmol) was added in small portions at a time at room temperature (internal temperature increase), and the mixture was stirred for 30 minutes. Water was added to the reaction solution, extraction was performed ethyl acetate, the extract was washed with saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was adsorbed onto silica gel and purified by silica gel column chromatography (hexane-ethyl acetate) to obtain the title compound (4.364 g, 19.20 mmol, 62.49%) as a brown oil.

Aufarbeitung

  1. additionwas added
  2. additionwas added in small portions at a time at room temperature
  3. temperature(internal temperature increase)
  4. stirringthe mixture was stirred for 30 minutes
  5. washthe extract was washed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. custompurified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-868b6d69f9df4049ab99b8686cccfd50
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372981B2

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