Potassium Carbonate → 3-Methoxy-4-methylaniline

HRID 1790206Notes

Reaction equation

HRID 1790206 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[O:11][CH3:12].O.O.[Sn](Cl)Cl.C([O-])([O-])=O.[K+].[K+]>C(OCC)(=O)C.C(O)C>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:2]=1[CH3:1])[NH2:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 61436Stannous chloride dihydrateHCID 83159Benzene, 2-methoxy-1-methyl-4-nitro-

Product 1

HCID 278823-Methoxy-4-methylanilineYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-methyl-5-nitroanisole (11.56 g, 69.2 mmol) in a mixture of ethyl acetate (200 mL) and ethanol (70 mL) was added portionwise tin (II) chloride dihydrate (109 g, 0.483 mol) and the mixture was stirred at room temperature overnight. The reaction mixture was basified with aq. K2CO3 and filtered over celite. The layers were separated. The aqueous layer was further extracted with ethyl acetate and the combined organics washed successively with water and brine, dried over MgSO4, filtered and evaporated to give 8.02 g of 3-methoxy-4-methyl-aniline (86% yield). 1H NMR (300 MHz; CDCl3): 2.09 (s, 3 H), 3.76 (s, 3 H), 4.01 (br s, 1 H), 6.20 (m, 2 H), 6.90 (d, J=8.4 Hz, 1 H).

Workup

  1. filtrationfiltered over celite
  2. customThe layers were separated
  3. extractionThe aqueous layer was further extracted with ethyl acetate
  4. washthe combined organics washed successively with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c885315dcbe54d788919632571ee7f87
Source dataset
uspto-grants-2006_07
Patent number
US07071218B2

Reaction notes

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