Potassium Hydroxide → 2-Chloro-3,5-Dimethoxyaniline

HRID 58176

Reaktionsgleichung

Reaktionsgleichung von HRID 58176
[OH-].[K+].[Cl:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([O:12][CH3:13])=[CH:6][C:5]=1[NH:14]C(=O)C>CCO.O>[Cl:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([O:12][CH3:13])=[CH:6][C:5]=1[NH2:14]

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 56594868N-(2-chloro-3,5-dimethoxyphenyl)acetamide

Produkt 1

HCID 227430742-Chloro-3,5-DimethoxyanilineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Potassium hydroxide (2.19 g, 39.18 mmol) was added to a solution of N-(2-chloro-3,5-dimethoxyphenyl)acetamide (1.8 g, 7.837 mmol) in EtOH (100 mL) and water (10 mL) and the reaction mixture heated to reflux for 12 h. Excess EtOH was removed under reduced pressure to obtain a residue. The residue was then partitioned between water and diethyl ether. The organic layer was separated, dried over sodium sulfate, filtered and concentrated under vacuum to afford the title compound (1.2 g, 82% of yield) as a white solid. 1HNMR (CDCl3, 300 MHz): δ 5.97 (s, 2H), 4.08 (brs, 2H), 3.84 (s, 3H), 3.75 (s, 3H); MS (ESI): 188.1 [M+H]+.

Aufarbeitung

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 12 h
  3. customExcess EtOH was removed under reduced pressure
  4. customto obtain a residue
  5. customThe residue was then partitioned between water and diethyl ether
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e54c098ae5e44c79abbbc706661fc090
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434697B2

Verknüpfte Notizen

Wird geladen…