Sodium Hydroxide → HCID 58307340, compound

HRID 448346Notes

Reaction equation

HRID 448346 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[C:5](=[C:10]([NH:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>C(O)C>[CH:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[NH:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:4]([C:3]([OH:25])=[O:2])[C:5]=1[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58307335HCID 58307335, compound

Product 1

HCID 58307340HCID 58307340, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(naphthalen-2-ylamino)phthalic acid dimethyl ester (0.75 g, 2.2 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 0.64 g in 93% yield: 1H NMR (DMSO-d6) δ 7.29-7.54 (m, 7H), 7.68 (d, J=8.1 Hz, 1H), 7.76-7.81 (m, 2H), 8.16 (br, 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
  11. customproviding 0.64 g in 93% yield

Sources & evidence

ORD record
ord-2f0f8ef3337d470baa0f795ee81d31fa
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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