Sodium Hydroxide → HCID 20130021, compound

HRID 448312Notes

Reaction equation

HRID 448312 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[C:5](=[C:10]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>C(O)C>[C:15]1([NH:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:4]([C:3]([OH:21])=[O:2])[C:5]=2[C:6]([OH:8])=[O:7])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58307348HCID 58307348, compound

Product 1

HCID 20130021HCID 20130021, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-phenylaminophthalic acid dimethyl ester (0.60 g, 2.1 mmol) and 3N NaOH (50 mL) in ethanol (100 mL) was heated to reflux for 2.5 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 0.52 g of the product in 97% yield: 1H NMR (DMSO-d6) δ 6.92 (t, J=7.3 Hz, 1H), 7.06-7.09 (m, 2H), 7.18-7.29 (m, 3H), 7.33-7.42 (m, 2H), 7.98 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2.5 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-01b122ea2d004532b430b50aa7cf7063
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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