Ethanol → HCID 59804293, compound

HRID 422026Notes

Reaction equation

HRID 422026 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)=[CH:6][C:5]=1[CH2:20][C:21]([OH:23])=[O:22])([O-:3])=[O:2].OS(O)(=O)=O.[CH3:29][CH2:30]O>>[CH2:29]([O:22][C:21](=[O:23])[CH2:20][C:5]1[CH:6]=[C:7]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[CH3:30]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 59804376HCID 59804376, compound

Product 1

HCID 59804293HCID 59804293, compound

Procedure

A solution of [2-nitro-5-(3-nitro-phenylamino)-phenyl]-acetic acid (0.49 g, 1.5 mmol) in EtOH (20 ml) is refluxed in the presence of 0.2 ml concentrated H2SO4 for 3 hours before it is concentrated. To the residue is added saturated NaHCO3. The mixture is extracted with ethyl acetate (30 ml×3). The organic layers are combined and dried with Na2SO4 to give [2-nitro-5-(3-nitro-phenylamino)-phenyl]-acetic acid ethyl ester: LC-MS: 346.0 (MH+).

Workup

  1. concentrationis concentrated
  2. additionTo the residue is added saturated NaHCO3
  3. extractionThe mixture is extracted with ethyl acetate (30 ml×3)
  4. dry with materialdried with Na2SO4

Sources & evidence

ORD record
ord-6270a8d8e5d444d5af05947736b6ecd8
Source dataset
uspto-grants-2012_01
Patent number
US08101608B2

Reaction notes

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