Ethanol → [2-Nitro-3-(3-nitro-phenylamino)-phenyl]-acetic acid ethyl ester

HRID 422018Notes

Reaction equation

HRID 422018 reaction equation
[N+:1]([C:4]1[C:9]([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:7]=[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]=[CH:7][CH:8]=[C:9]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:4]=1[N+:1]([O-:3])=[O:2])[CH3:30]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 59804360HCID 59804360, compound

Product 1

HCID 59804286[2-Nitro-3-(3-nitro-phenylamino)-phenyl]-acetic acid ethyl ester

Procedure

[2-Nitro-3-(3-nitro-phenylamino)-phenyl]-acetic acid (0.79 g, 2.5 mmol) is refluxed in EtOH (50 ml) in the presence of 0.5 ml concentrated H2SO4 for 2 hours. It is then concentrated and 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 the desired compound after concentration: 1H NMR (CDCl3) δ 1.29 (t, 3H, J=7.2 Hz), 3.92 (s, 2H), 4.20 (q, 2H, J=7.2 Hz), 6.89 (d, 1H, J=6.0 Hz), 7.34-7.41 (m, 2H), 7.44-7.52 (m, 2H), 7.92 (d, 1H, J=7.6 Hz), 8.03 (s, 1H), 8.17 (s, 1H); LC-MS: 346.0 (MH+).

Workup

  1. concentrationIt is then concentrated and to the residue
  2. additionis 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-da9c4635b98e4f3ea4ae55addbc0ca88
Source dataset
uspto-grants-2012_01
Patent number
US08101608B2

Reaction notes

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