Sodium Hydroxide → HCID 58307244, compound

HRID 448410Notes

Reaction equation

HRID 448410 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[C:5](=[C:10]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>C(O)C>[CH3:22][O:21][C:17]1[CH:16]=[C:15]([NH:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:4]([C:3]([OH:23])=[O:2])[C:5]=2[C:6]([OH:8])=[O:7])[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 583072403-(3-Methoxy-phenylamino)-phthalic acid dimethyl ester

Product 1

HCID 58307244HCID 58307244, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(3-methoxy-phenylamino)-phthalic acid dimethyl ester (0.43 g, 1.4 mmol) and 3N NaOH (25 mL) in ethanol (50 mL) was heated to reflux for 2 hours and cooled to room temperature. The solvent was removed under vacuum and the residue was dissolved in water (50 mL), washed with CH2Cl2 (2×50 mL), and acidified with 6N HCl to pH 1-2. The resulting mixture was extracted with ethyl acetate (2×50 mL). The organic extracts were washed with water (2×50 mL) and dried (MgSO4). After filtration of the MgSO4, the solvent was evaporated in vacuo to give the product, 0.32 g, 82% yield; 1H NMR (DMSO-d6) δ 3.70 (s, 3H), 6.48 (dd, J=7.9 Hz, J=1.7 Hz, 1H), 6.62-6.64 (m, 2H), 7.11-7.44 (m, 4H), 7.92 (s, 1H), 13.12 (br, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. customThe solvent was removed under vacuum
  4. dissolutionthe residue was dissolved in water (50 mL)
  5. washwashed with CH2Cl2 (2×50 mL)
  6. extractionThe resulting mixture was extracted with ethyl acetate (2×50 mL)
  7. washThe organic extracts were washed with water (2×50 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationAfter filtration of the MgSO4
  10. customthe solvent was evaporated in vacuo
  11. customto give the product, 0.32 g, 82% yield

Sources & evidence

ORD record
ord-8e0abf9a64344263aab8770d67200e1e
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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