Water → Ethyl (4-amino-3-nitrophenoxy)acetate

HRID 1647878Notes

Reaction equation

HRID 1647878 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CC(C)([O-])C.[K+].[CH2:18]([O:20][C:21](=[O:24])[CH2:22]Br)[CH3:19].O>CN(C)C=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:22][C:21]([O:20][CH2:18][CH3:19])=[O:24])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 37588824-Amino-3-NitrophenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 53821533Ethyl (4-amino-3-nitrophenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

25 g of 4-amino-3-nitro-phenol are dissolved in 250 ml of dimethylformamide and 18.5 g of potassium tert.butoxide are added in batches whilst cooling with ice. The mixture is stirred for a further 1.5 hours, then 18.5 ml of ethylbromoacetate are added dropwise, whilst cooling with water, and the mixture is stirred for a further 16 hours at ambient temperature. The solvent is evaporated off in vacuo and the residue is taken up with a mixture of 500 ml of ethyl acetate, 250 ml of tetrahydrofuran and 750 ml of water and the organic phase is washed with saturated saline solution. The aqueous phases are extracted with ethyl acetate, the organic phases are combined and evaporated down and the residue is purified by column chromatography (neutral aluminium oxide; eluant:methylene chloride). Yield: 29 g (75% of theory),

Workup

  1. temperaturewhilst cooling with ice
  2. stirringthe mixture is stirred for a further 16 hours at ambient temperature
  3. customThe solvent is evaporated off in vacuo
  4. additionthe residue is taken up with a mixture of 500 ml of ethyl acetate, 250 ml of tetrahydrofuran and 750 ml of water
  5. washthe organic phase is washed with saturated saline solution
  6. extractionThe aqueous phases are extracted with ethyl acetate
  7. customevaporated down
  8. customthe residue is purified by column chromatography (neutral aluminium oxide; eluant:methylene chloride)

Sources & evidence

ORD record
ord-8b5d3987335944519edf13b711f5ca9c
Source dataset
uspto-grants-1995_07
Patent number
US05434150

Reaction notes

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