Sodium Hydroxide → HCID 58307299, compound

HRID 448315Notes

Reaction equation

HRID 448315 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[C:5](=[C:10]([NH:14][C:15]2[CH:20]=[CH:19][C:18]3[O:21][CH2:22][O:23][C:17]=3[CH:16]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>C(O)C>[CH2:22]1[O:21][C:18]2[CH:19]=[CH:20][C:15]([NH:14][C:10]3[CH:11]=[CH:12][CH:13]=[C:4]([C:3]([OH:24])=[O:2])[C:5]=3[C:6]([OH:8])=[O:7])=[CH:16][C:17]=2[O:23]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58307277HCID 58307277, compound

Product 1

HCID 58307299HCID 58307299, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(3,4-methylenedioxyphenylamino)phthalic acid dimethyl ester (0.63 g, 1.9 mmol) and 3N NaOH (50 mL) in ethanol (100 mL) was heated to reflux for 2 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 0.50 g of the product in 88% yield: 1H NMR (DMSO-d6) δ 5.99 (s, 2H), 6.59 (dd, J=8.7 Hz, J=2.1 Hz, 1H), 6.77 (d, J=2.1 Hz, 1H), 6.85 (d, J=8.7 Hz, 1H), 7.04 (dd, J=7.3 Hz, J=0.9 Hz, 1H), 7.13 (dd, J=8.5 Hz, J=0.9 Hz, 1H), 7.31 (t, J=7.9 Hz, 1H), 7.95 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 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-ec724eed963943808321ff91e338ae94
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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