Hydrochloric Acid → 3-hydroxy-N-(2-hydroxyphenyl)benzamide

HRID 1883697

Reaction equation

HRID 1883697 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15]C)=[O:7].Cl.N1C=CC=CC=1.Cl>>[OH:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])=[O:7]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 9028663-methoxy-N-(2-methoxyphenyl)benzamideHCID 10176127Pyridinium chloride

Product 1

HCID 235084853-hydroxy-N-(2-hydroxyphenyl)benzamideYield 27.1%

Conditions

Temperature
190 °C

Procedure

451 mg of 3-methoxy-N-(2-methoxyphenyl)benzamide and 1.58 g of pyridine hydrochloride were mixed, and stirred on an oil bath at 190° C. for 2 hours. After cooling, dilute hydrochloric acid was added to the reaction mixture, and the product was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium hydrogen carbonate and dried over anhydrous sodium sulfate. After the solvent was distilled oft the resulting crude product was recrystallized from methanol to obtain 109 mg of 3-hydroxy-N-(2-hydroxyphenyl)benzamide.

Workup

  1. temperatureAfter cooling
  2. extractionthe product was extracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous solution of sodium hydrogen carbonate
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationAfter the solvent was distilled oft the resulting crude product
  6. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-6e4d1a4308d040539db3d1486d9713c0
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Linked notes

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