Sodium Hydroxide → HCID 67019673, compound

HRID 331537Notes

Reaction equation

HRID 331537 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[C:5](=[CH:10][C:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>C(O)C>[Cl:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=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:23])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 670196584-(3-Chloro-benzylamino)-phthalic acid dimethyl ester

Product 1

HCID 67019673HCID 67019673, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(3-chloro-benzylamino)-phthalic acid dimethyl ester (1.10 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 organic phase was washed with water (2×100 mL), dried (MgSO4), and evaporated, providing 1.00 g of 4-(3-chloro-benzylamino)-phthalic acid, in 99% yield; 1H NMR (DMSO-d6) δ 4.37 (d, J=5.7 Hz, 2H), 6.59-6.62 (m, 2H), 7.18 (t, J=6.0 Hz, 1H), 7.28-7.39 (m, 4H), 7.56-7.61 (m, 1H), 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

Sources & evidence

ORD record
ord-0007ff037b28429eb4e25b67a383aa1c
Source dataset
uspto-grants-2014_11
Patent number
US08877780B2

Reaction notes

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