Sodium Hydroxide → 4-[(Benzofuran-2-ylmethyl)amino]-phthalic acid

HRID 331538Notes

Reaction equation

HRID 331538 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[C:5](=[CH:10][C:11]([NH:14][CH2:15][C:16]2[O:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[CH:20]=2)=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>C(O)C>[O:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[CH:20]=[C:16]1[CH2:15][NH:14][C:11]1[CH:10]=[C:5]([C:6]([OH:8])=[O:7])[C:4](=[CH:13][CH:12]=1)[C:3]([OH:25])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67019667Dimethyl 4-[(1-benzofuran-2-ylmethyl)amino]phthalate

Product 1

HCID 670196574-[(Benzofuran-2-ylmethyl)amino]-phthalic acidYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[(benzofuran-2-ylmethyl)-amino]-phthalic acid dimethyl ester (0.89 g, 3.30 mmol) and 3N sodium hydroxide (50 mL) in ethanol (100 mL) was refluxed for one hour. The reaction mixture was cooled to room temperature, and the solvent was removed under vacuum. The residue was dissolved in water (100 mL), washed with CH2Cl2 (2×100 mL), and acidified (HCl). The resulting mixture was extracted with ethyl acetate (2×100 mL), and the combined organic layers were washed with water (2×100 mL), dried (MgSO4), and evaporated, providing 0.80 g of 4-[(benzofuran-2-ylmethyl)amino]-phthalic acid, in 98% yield; 1H NMR (DMSO-d6) δ 4.54 (d, J=4.5 Hz, 2H), 6.71-6.77 (m, 3H), 7.18-7.29 (m, 3H), 7.51-7.61 (m, 3H), 12.52 (br, 2H).

Workup

  1. temperaturewas refluxed for one hour
  2. customthe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in water (100 mL)
  4. washwashed with CH2Cl2 (2×100 mL)
  5. extractionThe resulting mixture was extracted with ethyl acetate (2×100 mL)
  6. washthe combined organic layers were washed with water (2×100 mL)
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-10fc3ee0dcb148299aa74e703d522bbd
Source dataset
uspto-grants-2014_11
Patent number
US08877780B2

Reaction notes

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