Sodium Hydroxide → HCID 67019688, compound

HRID 331536Notes

Reaction equation

HRID 331536 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[C:5](=[CH:10][C:11]([NH:14][CH2:15][C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>C(O)C>[O:17]1[CH:18]=[CH:19][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:21])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67019694Dimethyl 4-[(2-furylmethyl)amino]phthalate

Product 1

HCID 67019688HCID 67019688, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[(furan-2-ylmethyl)-amino]-phthalic acid dimethyl ester (1.11 g, 3.84 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 organic phase was washed with water (2×100 mL), and dried (MgSO4) and evaporated. The resulting solid was stirred in ether for 2 hours. The solid was filtered to give the 0.44 g of 4-[(furan-2-ylmethyl)-amino]-phthalic acid, in 44% yield; 1H NMR (DMSO-d6) δ 4.33 (d, J=5.1 Hz, 2H), 6.31 (d, J=3.0 Hz, 1H), 6.39 (dd, J=3.0 Hz, 1.8 Hz, 1H), 6.65-6.71 (m, 2H), 7.00 (t, J=5.7 Hz, 1H), 7.57-7.60 (m, 2H), 12.51 (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 organic phase was washed with water (2×100 mL)
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-12facb2d1f1a40829ce43df24c5a5358
Source dataset
uspto-grants-2014_11
Patent number
US08877780B2

Reaction notes

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