Potassium Carbonate → 3-Methoxy-4-methylaniline

HRID 2212603Notes

Reaction equation

HRID 2212603 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-0debac7a70a24722a741fb0fb2f2d96e
Source dataset
uspto-grants-2006_09
Patent number
US07102000B2

Reaction notes

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