Sodium Hydroxide → HCID 58307134, compound

HRID 448318Notes

Reaction equation

HRID 448318 reaction equation
C[O:2][C:3](=[O:25])[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][CH3:24])[CH:16]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>C(O)C>[CH3:24][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:25])=[O:2])[C:5]=2[C:6]([OH:8])=[O:7])[CH:20]=[CH:19][C:18]=1[O:21][CH3:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58307297HCID 58307297, compound

Product 1

HCID 58307134HCID 58307134, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(3,4-dimethoxyphenylamino)phthalic acid dimethyl ester (0.80 g, 2.3 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 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 0.59 g of the product in 81% yield: 1H NMR (DMSO-d6) δ 3.72 (s, 6H), 6.68 (dd, J=8.6 Hz, J=2.4 Hz, 1H), 6.81 (d, J=2.4 Hz, 1H), 6.90 (d, J=8.6 Hz, 1H), 7.00 (d, J=7.3 Hz, 1H), 7.16 (d, J=8.4 Hz, 1H), 7.30 (t, J=7.9 Hz, 1H), 7.98 (br, 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 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-bd6ff6e71df04359b168ecfca2cf60f3
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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