Hydrochloric Acid → Oxanilic acid

HRID 1968426Notes

Reaction equation

HRID 1968426 reaction equation
[C:1]([O:12]CC)(=[O:11])[C:2]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[OH-].[Na+].Cl.C(OCC)(=O)C>C1COCC1>[C:5]1([NH:4][C:2](=[O:3])[C:1]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 73826Ethyl oxanilate

Product 1

HCID 10378Oxanilic acidYield 83.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl oxanilate 83 (Aldrich, 1.0 g, 1.0 eq) in 12 mL of THF was treated dropwise with a 1N NaOH solution (5.70 mL, 1.1 eq) resulting in a white precipitate. After stirring for 3 hours at RT, 0.5N HCl and ethyl acetate were added, the organic layer separated, washed with 0.5N HCl and brine and then dried over sodium sulfate, filtered, and concentrated to give 712 mg (68%) of N-phenyl oxalamic acid 84 as a white solid with consistent analytical data. FIA M+H=166.0, M−H=163.9; 1H NMR (DMSO-d6) δ 10.70 (s, 1H), 7.75 (m, 2H), 7.35 (m, 2H), 7.15 (m, 1H) ppm.

Workup

  1. customresulting in a white precipitate
  2. customthe organic layer separated
  3. washwashed with 0.5N HCl and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e5c552b149d041ac8a579b2f6dbdb3ad
Source dataset
uspto-grants-2013_04
Patent number
US08426359B2

Reaction notes

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