Methanol → HCID 67343871, compound

HRID 1673360Notes

Reaction equation

HRID 1673360 reaction equation
CO.[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]=[C:4]1[C:12]1[CH:24]=[CH:23][C:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[C:14]([N+:25]([O-])=O)[CH:13]=1>[Fe].C(O)(=O)C>[NH2:25][C:14]1[CH:13]=[C:12]([C:4]2[O:3][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[CH:5]=2)[CH:24]=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

5

Reactant 2

HCID 887MethanolHCID 67342892HCID 67342892, compound

Product 1

HCID 67343871HCID 67343871, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

0.69 g of iron powder was added to a suspension of 7.0 mL of methanol and 7.0 mL of acetic acid containing 1.4 g of tert-butyl 4-(benzofuran-2-yl)-2-nitrobenzoate and the resulting mixture was heated to reflux for 2 hours. After the reaction mixture was cooled to room temperature, the solvent was evaporated under reduced pressure. A saturated sodium hydrogen carbonate aqueous solution and ethyl acetate were added to the obtained residue and insoluble were removed by filtration. 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 0.88 g of tert-butyl 2-amino-4-(benzofuran-2-yl)benzoate as white solid.

Workup

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

Sources & evidence

ORD record
ord-a2157e9e43c94a97b52b2d01e9e2b5d2
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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