Ethanol → Benzeneacetic acid, 2,4-dinitro-, ethyl ester

HRID 1246968Notes

Reaction equation

HRID 1246968 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][C:14]([OH:16])=[O:15])([O-:3])=[O:2].OS(O)(=O)=O.[CH3:22][CH2:23]O>>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][C:14]([O:16][CH2:22][CH3:23])=[O:15])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 2215132,4-Dinitrophenylacetic acid

Product 1

HCID 106546Benzeneacetic acid, 2,4-dinitro-, ethyl ester

Procedure

A mixture of 2,4-dinitrophenylacetic acid (10 g) and H2SO4 (0.1 eq) in EtOH (300 ml) was refluxed overnight. The solvent was evaporated, and EtOAc (150 ml) and H2O (200 ml) were added. The solution was extracted three times with EtOAc and washed with H2O followed by brine, dried over Na2SO4 and evaporated to give ethyl 2-(2,4-dinitrophenyl)acetate for next step without further purification. The above compound (5 g) was mixed with Pd—C (10%, 500 mg) in EtOH (200 ml) and hydrogenated under H2 atmosphere overnight. The reaction was filtered through Celite and evaporated. The residue was washed with EtOAc and filtered to give 6-aminoindolin-2-one.

Workup

  1. temperaturewas refluxed overnight
  2. customThe solvent was evaporated
  3. additionEtOAc (150 ml) and H2O (200 ml) were added
  4. extractionThe solution was extracted three times with EtOAc
  5. washwashed with H2O
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-12a4527458724af8aa9d420e88973b19
Source dataset
uspto-grants-2006_10
Patent number
US07129252B2

Reaction notes

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