Hydrochloric Acid → 2-Hexyloxy-4-nitroaniline

HRID 18867Notes

Reaction equation

HRID 18867 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[OH:13].CS(Cl)(=O)=O.Cl.[OH-].[Na+]>CN(C=O)C.O>[CH2:8]([O:13][C:5]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:4]=1[NH2:3])[CH2:9][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 116587522-Hexyloxy-4-nitroaniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

General Procedure for the Preparation of the base compound and Compounds 9-16. NaH (95% powder, 0.265 g, 10.5 mmol, 3.5 equiv) was added to a solution of alkyl instituted 2-amino-5-nitrophenol (3.0 mmol) in anhydrous DMF (8 mL) at room temperature. After being stirred at the same temperature for 30 min, MsCl (1.031 g, 9.0 mmol, 3 equiv) was added to the mixture, and the stirring was continued overnight at room temperature. H2O was added to the mixture, and then it was neutralized with 5 N HCl until pH=1-2. The intermediate precipitated as a yellow solid. It was collected by filtration and washed with H2O, which was used to the next reaction without further purification. The intermediate was added to a 3 N NaOH aq solution and was stirred at 80-90° C. overnight. After being cooled, it was neutralized with 5 N HCl until pH=1-2. The precipitated solid was collected and washed with H2O and cold ether to provide the desired product, and then it was recrystallized from ethyl acetate/hexane.

Workup

  1. customat room temperature
  2. waitthe stirring was continued overnight at room temperature
  3. customThe intermediate precipitated as a yellow solid
  4. filtrationIt was collected by filtration
  5. washwashed with H2O, which
  6. customwas used to the next reaction without further purification
  7. stirringwas stirred at 80-90° C. overnight
  8. temperatureAfter being cooled
  9. customThe precipitated solid was collected
  10. washwashed with H2O and cold ether

Sources & evidence

ORD record
ord-5831fa5dda914c0db8323de36ed840f9
Source dataset
uspto-grants-2010_06
Patent number
US07741520B2

Reaction notes

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