Methanol → 800375-15-9

HRID 1673335Notes

Reaction equation

HRID 1673335 reaction equation
CO.[N+:3]([C:6]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])([O-])=O>[Fe].C(O)(=O)C>[NH2:3][C:6]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 2

HCID 887MethanolHCID 57423400HCID 57423400, compound

Product 1

HCID 53412316800375-15-9

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

3.1 g of iron powder was added to a mixed solution of 24 mL of methanol and 24 mL of acetic acid containing 4.8 g of methyl 2-nitro-4-phenylbenzoate, and the resulting mixture was heated to reflux for 2 hours. After the reaction mixture was cooled to room temperature, insoluble were removed by filtration and a saturated sodium hydrogen carbonate aqueous solution and ethyl acetate added to the filtrate. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure, Hexane was added to the obtained residue and a solid substance was separated by filtration to obtain 1.8 g of methyl 2-amino-4-phenylbenzoate as white solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. custominsoluble were removed by filtration
  4. additiona saturated sodium hydrogen carbonate aqueous solution and ethyl acetate added to the filtrate
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. washafter washed with a saturated sodium hydrogen carbonate aqueous solution
  8. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure, Hexane
  9. additionwas added to the obtained residue
  10. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-58b7e14efa364df4bc4792451c01ffd6
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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