Sodium Bicarbonate → 2,4,5-Trimethoxyaniline

HRID 601013

Reaktionsgleichung

Reaktionsgleichung von HRID 601013
[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-a6b536d91ec94f6fbd89326ad637e0d7
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902239B2

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