Sodium Hydroxide → 7-(Cyclopropylmethoxy)naphthalene-1-amine

HRID 260669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 260669
[CH:1]1([CH2:4][O:5][C:6]2[CH:15]=[C:14]3[C:9]([CH:10]=[CH:11][CH:12]=[C:13]3[NH:16]C(=O)C)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>COCCO>[CH:1]1([CH2:4][O:5][C:6]2[CH:15]=[C:14]3[C:9]([CH:10]=[CH:11][CH:12]=[C:13]3[NH2:16])=[CH:8][CH:7]=2)[CH2:2][CH2:3]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 22400263N-[7-(Cyclopropylmethoxy)naphth-1-yl]acetamide

Produkt 1

HCID 224002667-(Cyclopropylmethoxy)naphthalene-1-amineAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80192-MethoxyethanolLösungsmittel

Versuchsvorschrift

A mixture of 13 g (0.05 mol) of N-[7-(cyclopropylmethoxy)naphth-1-yl]acetamide, 35 ml of 10N sodium hydroxide solution and 150 ml of 2-methoxyethanol is heated at reflux for 4 h under a nitrogen atmosphere. The solvent is evaporated under reduced pressure. The residue is taken up in 200 ml of dichloromethane and 200 ml of water, and the mixture is stirred in the presence of carbon black and filtered over kieselguhr. The organic phase obtained is separated, dried over magnesium sulphate and filtered. The solvent is evaporated under reduced pressure and the residue is purified by chromatography on a column of silica gel, eluting with dichloromethane. 7.8 g of an oil are obtained which crystallizes on cooling to give a product, melting point: 49°-50° C.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 4 h under a nitrogen atmosphere
  3. customThe solvent is evaporated under reduced pressure
  4. filtrationfiltered over kieselguhr
  5. customThe organic phase obtained
  6. customis separated
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. customThe solvent is evaporated under reduced pressure
  10. customthe residue is purified by chromatography on a column of silica gel
  11. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-9ee070b9b67f4ef7b6611f7174f33921
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05530002

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