Sodium Bicarbonate → 2,4,5-Trimethoxyaniline

HRID 1179221

Reaction equation

HRID 1179221 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 124101382,4,5-TrimethoxyanilineYield 54.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-461be6b146f247cdbf5c32786dd4c938
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Linked notes

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