Potassium Hydroxide → 2-(4-Methoxy-3-nitrophenylamino)ethanol

HRID 751544Notes

Reaction equation

HRID 751544 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][O:13]C2=O)=[CH:7][C:6]=1[N+:17]([O-:19])=[O:18]>CO.O>[OH:13][CH2:14][CH2:15][NH:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[C:6]([N+:17]([O-:19])=[O:18])[CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 25110856HCID 25110856, compound

Product 1

HCID 144537412-(4-Methoxy-3-nitrophenylamino)ethanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Solid potassium hydroxide (3.5 g) is dissolved in methanol (100 ml). To the obtained solution the 3-(4-methoxy-3-nitrophenyl)-1,3-oxazolidin-2-one of step 1.1 (5 g) is added whereupon a yellow suspension is formed. Then the reaction mixture is heated under reflux for 5 hours and a red solution is obtained. With stirring, diluted acetc acid (3.7 g in 20 ml water) is added dropwise to the warm solution and the reaction mixture is cooled down to from about 0° C. to about 5° C. An orange suspension is obtained, which is filtered. The resulting solid is dried.

Workup

  1. customis formed
  2. temperatureThen the reaction mixture is heated
  3. temperatureunder reflux for 5 hours
  4. customa red solution is obtained
  5. additionis added dropwise to the warm solution
  6. temperaturethe reaction mixture is cooled down to from about 0° C. to about 5° C
  7. customAn orange suspension is obtained
  8. filtrationwhich is filtered
  9. customThe resulting solid is dried

Sources & evidence

ORD record
ord-921f4043ed644bae89bd5c61a19d4735
Source dataset
uspto-grants-2008_07
Patent number
US07405325B2

Reaction notes

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