Methanol → Tert-butyl 3-amino-[1,1'-biphenyl]-4-carboxylate

HRID 2191621Notes

Reaction equation

HRID 2191621 reaction equation
CO.[N+:3]([C:6]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=[CH:15][C:7]=1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([O-])=O>[Fe].C(O)(=O)C>[NH2:3][C:6]1[CH:18]=[C:17]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:16]=[CH:15][C:7]=1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

5

Reactant 2

HCID 887MethanolHCID 68962230HCID 68962230, compound

Product 1

HCID 58508425Tert-butyl 3-amino-[1,1'-biphenyl]-4-carboxylateYield 48.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a suspension of methanol 38 mL and acetic acid 38 mL of tert-butyl 2-nitro-4-phenylbenzoate 7.5 g was added iron powder 4.2 g at room temperature, and it was heated and refluxed for 1 hour. After the reaction mixture was cooled to room temperature, the solvent was removed under reduced pressure. To the obtained residue, saturated sodium hydrogen carbonate aqueous solution and ethyl acetate were added, and insoluble matter was filtrated. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. Hexane was added to the obtained residue, solid matter was filtrated to give tert-butyl 2-amino-4-phenylbenzoate 3.3 g of white solid.

Workup

  1. temperatureit was heated
  2. temperaturerefluxed for 1 hour
  3. customthe solvent was removed under reduced pressure
  4. additionTo the obtained residue, saturated sodium hydrogen carbonate aqueous solution and ethyl acetate were added
  5. filtrationinsoluble matter was filtrated
  6. customThe organic layer was separated
  7. washafter sequential washing with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution
  8. customthe solvent was removed under reduced pressure
  9. additionHexane was added to the obtained residue, solid matter
  10. filtrationwas filtrated

Sources & evidence

ORD record
ord-2c5d333c15664492bb74ef8af69728fb
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

Loading…