Methanol → HCID 67344120, compound

HRID 1673362Notes

Reaction equation

HRID 1673362 reaction equation
CO.[CH3:3][O:4][C:5]1[CH:6]=[C:7](/[CH:11]=[CH:12]/[C:13]2[CH:25]=[CH:24][C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:15]([N+:26]([O-])=O)[CH:14]=2)[CH:8]=[CH:9][CH:10]=1>[Fe].C(O)(=O)C>[NH2:26][C:15]1[CH:14]=[C:13](/[CH:12]=[CH:11]/[C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH3:3])[CH:6]=2)[CH:25]=[CH:24][C:16]=1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]

Participants

5

Reactant 2

HCID 887MethanolHCID 67342987HCID 67342987, compound

Product 1

HCID 67344120HCID 67344120, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

0.70 g of iron powder was added to a suspension of 7.5 mL of methanol and 7.5 mL of acetic acid containing 1.5 g of tert-butyl 4-((E)-2-(3-methoxyphenyl)vinyl)-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. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=4:1] to obtain 0.44 g of tert-butyl 2-amino-4-((E)-2-(3-methoxyphenyl)vinyl)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. customThe obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=4:1]

Sources & evidence

ORD record
ord-07e64a9525b449a0ab3920b849fba4ae
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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