Sodium Hydroxide → 3-(4-Methoxy-2-phenoxy-phenylamino)-phthalic acid

HRID 448386Notes

Reaction equation

HRID 448386 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[C:5](=[C:10]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2[O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>C(O)C>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:4]([C:3]([OH:30])=[O:2])[C:5]=2[C:6]([OH:8])=[O:7])=[C:16]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 583071863-(4-Methoxy-2-phenoxy-phenylamino)-phthalic acid dimethyl ester

Product 1

HCID 583071663-(4-Methoxy-2-phenoxy-phenylamino)-phthalic acidYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(4-methoxy-2-phenoxy-phenylamino)-phthalic acid dimethyl ester (0.80 g, 2.0 mmol) and 3N NaOH (50 mL) in ethanol (100 mL) was heated to reflux for 90 minutes. The mixture was cooled, and the solvent was removed under vacuum. The residue was dissolved in water (100 mL), washed with CH2Cl2 (2×100 mL), and acidified (HCl). The resulting mixture was extracted with ethyl acetate (4×50 mL) and the combined extracts were washed with water (3×100 mL), dried (MgSO4) and evaporated, providing 0.69 g, in 93% yield; 1H NMR (DMSO-d6) δ 3.71 (s, 3H), 6.58 (d, J=2.7, 1H), 6.80 (dd, J=8.8 Hz, J=2.7 Hz, 1H), 6.88-6.94 (m, 3H), 7.03-7.10 (m, 2H), 7.27-7.36 (m, 4H), 8.07 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 90 minutes
  3. temperatureThe mixture was cooled
  4. customthe solvent was removed under vacuum
  5. dissolutionThe residue was dissolved in water (100 mL)
  6. washwashed with CH2Cl2 (2×100 mL)
  7. extractionThe resulting mixture was extracted with ethyl acetate (4×50 mL)
  8. washthe combined extracts were washed with water (3×100 mL)
  9. dry with materialdried (MgSO4)
  10. customevaporated
  11. customproviding 0.69 g

Sources & evidence

ORD record
ord-adc9ca98ec0842dab968953a8460d4b9
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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