2-Methoxyethanol → 4-Cyano-3-(2-methoxyethoxy)aniline

HRID 393582

Reaktionsgleichung

Reaktionsgleichung von HRID 393582
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][OH:7].[NH2:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11](Cl)[CH:10]=1>CN1C(=O)CCC1.O>[C:13]([C:12]1[CH:15]=[CH:16][C:9]([NH2:8])=[CH:10][C:11]=1[O:7][CH2:6][CH2:5][O:4][CH3:3])#[N:14]

Komponenten

6

Edukt 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 887284-Amino-2-chlorobenzonitrile

Produkt 1

HCID 226465404-Cyano-3-(2-methoxyethoxy)anilineAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Sodium hydride (300 mg of an 80% suspension in mineral oil, 10 mmol) was added to 2-methoxyethanol (0.76 g, 10 mmol) in NMP (5 ml) and the mixture stirred for 15 minutes. 4-Amino-2-chlorobenzonitrile (1.5 g, 10 mmol) was added and the mixture heated at 100° C. for 5 hours. The mixture was allowed to cool, diluted with water and extracted with ethyl acetate (3×50 ml). The combined extracts were dried (MgSO4) and the solvent removed by evaporation. The residue was purified by chromatography eluting with increasingly polar mixtures of methylene chloride/ethyl acetate to give 4-cyano-3-(2-methoxyethoxy)aniline (760 mg, 40%) as a dark yellow oil.

Aufarbeitung

  1. temperatureto cool
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customthe solvent removed by evaporation
  5. customThe residue was purified by chromatography
  6. washeluting
  7. temperaturewith increasingly polar mixtures of methylene chloride/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9e8d38ce1e9944648bfcdeff6518031c
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809097B1

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