Sodium Hydroxide → 3-(3-Hydroxy-4-methoxyphenylamino)phthalic acid

HRID 448343Notes

Reaction equation

HRID 448343 reaction equation
C[O:2][C:3](=[O:31])[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][Si](C(C)(C)C)(C)C)[CH:16]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>C(O)C>[OH:23][C:17]1[CH:16]=[C:15]([NH:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:4]([C:3]([OH:31])=[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 583073223-[3-(Tert-butyldimethylsilanyloxy)-4-methoxyphenyl-amino]phthalic acid dimethyl ester

Product 1

HCID 583071623-(3-Hydroxy-4-methoxyphenylamino)phthalic acidYield 97.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-[3-(tert-butyldimethylsilanyloxy)-4-methoxyphenyl-amino]phthalic acid dimethyl ester (1.0 g, 2.2 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 0.65 g of the product, in 96% yield: 1H NMR (DMSO-d6) δ 3.73 (s, 3H), 6.54 (dd, J=8.5 Hz, J=2.5 Hz, 1H), 6.60 (d, J=2.5 Hz, 1H), 6.86 (d, J=8.5 Hz, 1H), 6.98 (d, J=7.3 Hz, 1H), 7.13 (d, J=7.7 Hz, 1H), 7.30 (t, J=7.9 Hz, 1H), 7.93 (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-a4e389d888224d4ea97e1a1dcd8708ee
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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