Ethanol → HCID 58508576, compound

HRID 454530Notes

Reaction equation

HRID 454530 reaction equation
[Cl-].[NH4+].C(O)C.[O:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([N+:21]([O-])=O)[CH:12]=1>[Fe].O>[NH2:21][C:13]1[CH:12]=[C:11]([C:7]2[O:6][CH:10]=[CH:9][CH:8]=2)[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium Chloride2×HCID 58508528HCID 58508528, compound

Product 1

HCID 58508576HCID 58508576, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 962WaterSolvent2×

Procedure

Water (0.56 mL), ammonium chloride (18 mg), and iron powder (94 mg) were added to an ethanol (2.1 mL) suspension of methyl 4-(furan-2-yl)-2-nitrobenzoate (0.14 g), followed by heating to reflux for 2 hours and 30 minutes. The reaction mixture was cooled to room temperature, and then ammonium chloride (18 mg), iron powder (31 mg), and water (0.28 mL) were added thereto, followed by heating to reflux for 1 hour. The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. A saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the obtained residue, and the insoluble substance was removed by filtration. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 99-95% hexane/ethyl acetate] to obtain 78 mg of methyl 2-amino-4-(furan-2-yl)benzoate as a light yellow solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 2 hours and 30 minutes
  3. temperatureby heating
  4. temperatureto reflux for 1 hour
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customthe solvent was evaporated under reduced pressure
  7. additionA saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the obtained residue
  8. customthe insoluble substance was removed by filtration
  9. customThe organic layer was separated
  10. washwashed with a saturated aqueous solution of sodium chloride
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customthe solvent was evaporated under reduced pressure
  13. customThe obtained residue was purified by silica gel column chromatography [eluent: 99-95% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-f54d3e466edf4eb19383078b3634f959
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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