4-Aminophenol → 4-(3-Methylamino-4-nitrophenoxy)aniline

HRID 1294062Notes

Reaction equation

HRID 1294062 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH3:11][NH:12][C:13]1[CH:18]=[C:17](Cl)[CH:16]=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21]>CN(C=O)C>[CH3:11][NH:12][C:13]1[CH:18]=[C:17]([CH:16]=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21])[O:10][C:7]1[CH:8]=[CH:9][C:4]([NH2:3])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 24758Sodium hydrideHCID 2580415-chloro-N-methyl-2-nitroaniline2×

Product 1

HCID 177559824-(3-Methylamino-4-nitrophenoxy)anilineYield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
90 °C

Procedure

To a mixture of NaH (60% oily, 440 mg, 11.0 mmol) in DMF (30 mL) was added a solution of 4-aminophenol (1.20 g, 11.0 mmol) in DMF (15 mL) followed by N-methyl-5-chloro-2-nitroaniline (Intermediate 8D-2.02 g, 10.0 mmol) in DMF (20 mL). The mixture was stirred at 90° C. overnight. After cooling, the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4 then evaporated. Sequence purification on SiO2 column chromatography gave the title compound (2.44 g, 94%): MS m/e 260 (M+1).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customthen evaporated
  6. customSequence purification on SiO2 column chromatography

Sources & evidence

ORD record
ord-b8139bffaedd41898c072ab94436b63c
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

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