4-(Benzyloxy)-5-methoxy-2-nitrobenzamide → HCID 21699258, compound

HRID 1597253Notes

Reaction equation

HRID 1597253 reaction equation
C([O:8][C:9]1[C:17]([O:18][CH3:19])=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[C:11]([N+:20]([O-:22])=[O:21])[CH:10]=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[OH:8][C:9]1[C:17]([O:18][CH3:19])=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[C:11]([N+:20]([O-:22])=[O:21])[CH:10]=1

Participants

3

Reactant 1

HCID 216992834-(Benzyloxy)-5-methoxy-2-nitrobenzamide

Product 1

HCID 21699258HCID 21699258, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Procedure

4-Benzyloxy-5-methoxy-2-nitrobenzamide (26 g, 91 mmol), (J. Med. Chem. 1977, vol 20, 146-149), was dissolved in TFA and heated at reflux for 2 hours. After cooling the TFA was removed by evaporation and the residue was stirred with 2M sodium hydroxide and insoluble material was removed by filtration. The red aqueous solution was acified to pHl with concentrated hydrochloric acid and allowed to cool back to ambient temperature before collecting the product by filtration. The obtained solid was washed with water and ether and dried in a vacuum oven at 60° C. to give 4-hydroxy-5-methoxy-2-nitrobenzamide (11.04 g, 62%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customwas removed by evaporation
  4. customwas removed by filtration
  5. custombefore collecting the product
  6. filtrationby filtration
  7. washThe obtained solid was washed with water and ether
  8. customdried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-a3eaa03abf2e4895b3a68be31209ee6f
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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