Hydrazine hydrate (1:1) → 3,4,5-Trimethoxyaniline

HRID 1487215Notes

Reaction equation

HRID 1487215 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[C:5]([O:12][CH3:13])[C:4]=1[O:14][CH3:15].O.NN>C(O)C.[Pd]>[CH3:13][O:12][C:5]1[CH:6]=[C:7]([CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[O:14][CH3:15])[NH2:9]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2387701,2,3-Trimethoxy-5-nitrobenzene

Product 1

HCID 322853,4,5-TrimethoxyanilineYield 96.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1,2,3-trimethoxy-5-nitrobenzene (6.64 g, 31.2 mmol) in ethanol (250 mL) was added palladium on carbon (10%, 300 mg) and hydrazine hydrate (85%, 5.7 mL). After emission of gas has ceased, the reaction mixture was heated at refluxed for 1 hour, cooling to room temperature, filtered and evaporated to afford the product 3,4,5-trimethoxyaniline as a white solid (5.5 g, yield 96.4%). 1H NMR (400 MHz, DMSO-d6) δ ppm 5.86 (s, 2H), 4.82 (br, 2H), 3.64 (s, 6H), 3.50 (s, 3H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat refluxed for 1 hour
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-9c638a8684f44df59a297b370ae3ef1a
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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