Sodium Hydroxide → 3,5-Dichloro-4-methoxyaniline

HRID 3125

Reaktionsgleichung

Reaktionsgleichung von HRID 3125
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([Cl:11])[C:3]=1[O:12][CH3:13].O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([Cl:11])[C:3]=1[O:12][CH3:13])[NH2:8]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 3097161,3-Dichloro-2-methoxy-5-nitrobenzene

Produkt 1

HCID 131786513,5-Dichloro-4-methoxyanilineAusbeute 83,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A stirred mixture of 2,6-dichloro-4-nitroanisole (4.6 g, 21 mM) and tin(II) dichloride dihydrate (23.4 g, 104 mM) in ethanol (72 mL) was refluxed for 3 hr. After cooling to room temperature, the reaction mixture was poured into ice water which was then treated with 2N sodium hydroxide until the solution became basic. The resulting mixture was filtered through diatomaceous earth and the filtrate was extracted with ethyl acetate. The combined ethyl acetate extracts were dried (MgSO4), filtered and concentrated to obtain (3.33 g, 83.7%) the title compound as a yellow-brown solid, mp 80°-81° C.; MS(CI): 192 (M+H).

Aufarbeitung

  1. temperaturewas refluxed for 3 hr
  2. filtrationThe resulting mixture was filtered through diatomaceous earth
  3. extractionthe filtrate was extracted with ethyl acetate
  4. dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d1949a80f5a34ab9a1a505ee7b40c299
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733910

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