Potassium Hydroxide → Oxanilic acid

HRID 1244449Notes

Reaction equation

HRID 1244449 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:16])[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8])C>O.CO>[C:10]1([NH:9][C:7](=[O:8])[C:6]([OH:16])=[O:5])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 73826Ethyl oxanilate

Product 1

HCID 10378Oxanilic acidYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of KOH (1.68 g, 30 mmol) in water (25 mL) and MeOH (25 mL) was added to Intermediate 1 (5.8 g, 30 mmol), and the resulting mixture was stirred for 18 hours at room temperature. The reaction was diluted with water, then extracted with EtOAc. The aqueous layer was cooled in an ice bath, acidified with 1N HCl, extracted with EtOAc, dried (Na2SO4), and concentrated in vacuo to provide 3.8 g (77%) of a colorless solid. 1H NMR (DMSO-d6) δ: 7.1–7.8 (m, 6H), 10.5 (s, 1H); MS ES+m/e 166.0 (p+1), ES−m/e 164.1 (p−1). Anal. Calcd for C8H7NO3: C, 58.18; H, 4.27; N, 8.48. Found: C, 57.99; H, 4.25; N, 8.46.

Workup

  1. extractionextracted with EtOAc
  2. temperatureThe aqueous layer was cooled in an ice bath
  3. extractionextracted with EtOAc
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dcf235f64cc84c519f0b265f2b4d9fab
Source dataset
uspto-grants-2006_10
Patent number
US07122554B2

Reaction notes

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