Sodium Hydroxide → 3-(3-Ethoxy-4-methoxyphenylamino)phthalic acid

HRID 448338Notes

Reaction equation

HRID 448338 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[C:5](=[C:10]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH2:24][CH3:25])[CH:16]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>C(O)C>[CH2:24]([O:23][C:17]1[CH:16]=[C:15]([NH:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:4]([C:3]([OH:26])=[O:2])[C:5]=2[C:6]([OH:8])=[O:7])[CH:20]=[CH:19][C:18]=1[O:21][CH3:22])[CH3:25]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 583072013-(3-Ethoxy-4-methoxyphenylamino)phthalic acid dimethyl ester

Product 1

HCID 583071773-(3-Ethoxy-4-methoxyphenylamino)phthalic acidYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(3-ethoxy-4-methoxyphenylamino)phthalic acid dimethyl ester (0.85 g, 2.4 mmol) and 3N NaOH (50 mL) in ethanol (100 mL) was heated to reflux for 3 hours. The mixture was cooled, and the solvent was removed under vacuum. The residue was dissolved in water (100 mL), washed with ethyl acetate (3×75 mL), acidified (HCl) and extracted with ethyl acetate (3×75 mL). The combined organic extracts were washed with water (3×75 mL), dried (MgSO4), and evaporated, providing 0.68 g of the product, in 87% yield: 1H NMR (DMSO-d6) δ 1.31 (t, J=6.9 Hz, 3H), 3.73 (s, 3H), 3.96 (q, J=6.9, 2H), 6.69 (dd, J=8.6 Hz, J=2.4 Hz, 1H), 6.78 (d, J=2.4 Hz, 1H), 6.90 (d, J=8.6 Hz, 1H), 7.00 (d, J=7.2 Hz, 1H), 7.15 (d, J=8.0 Hz, 1H), 7.30 (t, J=7.9 Hz, 1H), 7.97 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. temperatureThe mixture was cooled
  4. customthe solvent was removed under vacuum
  5. dissolutionThe residue was dissolved in water (100 mL)
  6. washwashed with ethyl acetate (3×75 mL)
  7. extractionextracted with ethyl acetate (3×75 mL)
  8. washThe combined organic extracts were washed with water (3×75 mL)
  9. dry with materialdried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-6c31dfef3fa9407a865ae7cea721f7c3
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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