Water → (4-Methoxy-phenyl)-(2-methyl-6-nitro-phenyl)amine

HRID 2092933Notes

Reaction equation

HRID 2092933 reaction equation
F[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:11].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1.C(C)(C)C([O-])=O.[K+].O>CS(C)=O>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=2[CH3:11])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7732P-AnisidineHCID 134709572-Fluoro-1-methyl-3-nitrobenzeneHCID 23677462Potassium isobutyrate

Product 1

HCID 67528647(4-Methoxy-phenyl)-(2-methyl-6-nitro-phenyl)amineYield 42%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 50 g of 2-fluoro-3-nitrotoluene in 1.1 L of DMSO are added at room temperature 59.5 g of para-anisidine (1.5 equivalents). After 5 minutes of stirring at room temperature, 57.9 g of potassium tert-butanoate (1.6 equivalents) are added to the reaction medium and the whole is heated to 110° C. for 1 hour. The reaction medium is directly hydrolyzed by adding 1 L of ice and water and then the aqueous phase is extracted several times with ethyl acetate. The organic phases are collected, dried on sodium sulphate, filtered and then dry concentrated. The raw product is chromatographed on silica gel (ether/cyclohexane:0/100, 5/95 and then 20/80) in order to provide 34.95 g of the expected compound as a dark red solid.

Workup

  1. temperaturethe whole is heated to 110° C. for 1 hour
  2. extractionthe aqueous phase is extracted several times with ethyl acetate
  3. customThe organic phases are collected
  4. customdried on sodium sulphate
  5. filtrationfiltered
  6. customdry
  7. concentrationconcentrated
  8. customThe raw product is chromatographed on silica gel (ether/cyclohexane

Sources & evidence

ORD record
ord-c05fb29caece430f87dc0ce986753941
Source dataset
uspto-grants-2013_05
Patent number
US08440833B2

Reaction notes

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