Sodium Hydroxide → HCID 58307294, compound

HRID 448323Notes

Reaction equation

HRID 448323 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]([C:21]([CH3:24])([CH3:23])[CH3:22])=[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:21]([C:18]1[CH:17]=[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]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58307288HCID 58307288, compound

Product 1

HCID 58307294HCID 58307294, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(4-tert-butylphenylamino)phthalic acid dimethyl ester (0.70 g, 2.1 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. The brown residue was dissolved in 15 mL of 1:1 hexanes-ether. Addition of 35 mL hexanes resulted in precipitation of the product as a bright yellow solid, providing 0.50 g in 78% yield: 1H NMR (CDCl3) δ 1.33 (s, 9H), 7.11-7.15 (m, 3H), 7.33-7.39 (m, 4H).

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
  11. dissolutionThe brown residue was dissolved in 15 mL of 1:1 hexanes-ether
  12. additionAddition of 35 mL hexanes

Sources & evidence

ORD record
ord-1fa8d736699745629982b33bc3468355
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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