Sodium Bicarbonate → 2,4,5-Trimethoxyaniline

HRID 1179221

Reaktionsgleichung

Reaktionsgleichung von HRID 1179221
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([O:12][CH3:13])=[CH:5][C:4]=1[O:14][CH3:15].O.O.[Sn](Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH3:13][O:12][C:6]1[CH:5]=[C:4]([O:14][CH3:15])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[NH2:9]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 8224151,2,4-Trimethoxy-5-nitrobenzeneHCID 85782573Tin tetrachloride dihydrate

Produkt 1

HCID 124101382,4,5-TrimethoxyanilineAusbeute 54,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1,2,4-Trimethoxy-5-nitro-benzene (1.20 g, 5.63 mmol) and tin chloride dihydrate (3.81 g, 16.9 mmol) in ethyl acetate (50 mL) was stirred at 65-70° C. for 20 h. The reaction was cooled, carefully neutralized with sodium bicarbonate and was filtered through Celite. The organic phase was washed with brine, dried (sodium sulfate) and was evaporated. Purification by flash chromatography (SiO2) eluted with 3:7 ethyl acetate:hexanes provided 2,4,5-trimethoxy-phenylamine (0.56 g, 54% yield) as a tan solid. 1H-NMR (DMSO-d6, 500 MHz) 6.57 (s, 1H), 6.37 (s, 1H), 3.70 (s, 3H), 3.65 (s, 3H), 3.63 (s, 3H) ppm; HPLC (Method A) 2.163 min.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. filtrationwas filtered through Celite
  3. washThe organic phase was washed with brine
  4. dry with materialdried (sodium sulfate)
  5. customwas evaporated
  6. customPurification by flash chromatography (SiO2)
  7. washeluted with 3:7 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-461be6b146f247cdbf5c32786dd4c938
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279469B2

Verknüpfte Notizen

Wird geladen…