Sodium Hydroxide → HCID 18506150, compound

HRID 331535Notes

Reaction equation

HRID 331535 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[C:5](=[CH:10][C:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>C(O)C>[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:22])=[O:2])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 670196894-Benzylamino-phthalic acid dimethyl ester

Product 1

HCID 18506150HCID 18506150, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-benzylamino-phthalic acid dimethyl ester (1.11 g, 3.71 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), and resulting mixture was extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with water (2×100 mL), and dried (MgSO4) and evaporated under vacuum. The resulting solid was stirred in ether for 2 hours. The solid was filtered and dried, providing 0.50 g of 4-benzylamino-phthalic acid, in 74% yield; 1H NMR (DMSO-d6) δ 4.35 (d, J=5.7 Hz, 2H), 6.59-6.62 (m, 2H), 7.10-7.34 (m, 6H), 7.54-7.57 (m, 1H), 12.48 (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. customresulting mixture
  6. extractionwas extracted with ethyl acetate (2×100 mL)
  7. washThe combined organic extracts were washed with water (2×100 mL)
  8. dry with materialdried (MgSO4)
  9. customevaporated under vacuum
  10. filtrationThe solid was filtered
  11. customdried

Sources & evidence

ORD record
ord-39a8c04d3a92421d8b4f8d1c24cb9c90
Source dataset
uspto-grants-2014_11
Patent number
US08877780B2

Reaction notes

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