Acetic Acid → HCID 57879556, compound

HRID 1673406Notes

Reaction equation

HRID 1673406 reaction equation
CO.[C:3](O)(=O)[CH3:4].[N+:7]([C:10]1[CH:19]=[C:18]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])([O-])=O.[C:28](=[O:31])([O-])O.[Na+]>[Fe].C(OCC)(=O)C>[C:28]([NH:7][C:10]1[CH:19]=[C:18]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])(=[O:31])[C:4]1[CH:3]=[CH:12][CH:11]=[CH:10][CH:19]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 57667922HCID 57667922, compound

Product 1

HCID 57879556HCID 57879556, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Procedure

0.31 g of iron powder was added to a mixed solution of 5.3 mL of methanol and 1.6 mL of acetic acid containing 0.53 g of methyl 2-nitro-4-(phenoxymethyl)benzoate, and the resulting mixture was heated to reflux for 3 hours. The reaction mixture was cooled to room temperature and ethyl acetate and a saturated sodium hydrogen carbonate aqueous solution were added and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in 5.3 mL of methylene chloride and 0.51 mL of triethylamine and 0.26 mL of benzoyl chloride were added while ice-cooled sequentially and stirred at room temperature for 15 hours. The solvent was evaporated under reduced pressure and ethyl acetate and 1.0 mol/L hydrochloric acid were added to the obtained residue. The organic layer was separated and washed with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Hexane and diisopropyl ether were added to the obtained residue and a solid substance was separated by filtration to obtain 0.31 g of methyl 2-(benzamido)-4-(phenoxymethyl)benzoate as white solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 3 hours
  3. custominsoluble were removed by filtration
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. washafter washed with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution sequentially
  7. customthe solvent was evaporated under reduced pressure
  8. dissolutionThe obtained residue was dissolved in 5.3 mL of methylene chloride
  9. addition0.51 mL of triethylamine and 0.26 mL of benzoyl chloride were added while ice-
  10. temperaturecooled sequentially
  11. customThe solvent was evaporated under reduced pressure and ethyl acetate and 1.0 mol/L hydrochloric acid
  12. additionwere added to the obtained residue
  13. customThe organic layer was separated
  14. washwashed with saturated sodium chloride aqueous solution
  15. dry with materialdried over anhydrous magnesium sulfate
  16. customthe solvent was evaporated under reduced pressure
  17. additionHexane and diisopropyl ether were added to the obtained residue
  18. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-e24529db9bec4342860d4a33169a8b03
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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