Ethyl Acetate → HCID 66704060, compound

HRID 424787Notes

Reaction equation

HRID 424787 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=2[N+:19]([O-])=O)=[CH:7][CH:6]=1)=[O:4].C(OCC)(=O)C>C(O)C.[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=2[NH2:19])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 66704212HCID 66704212, compound

Product 1

HCID 66704060HCID 66704060, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 4′-methoxy-2′-nitro-biphenyl-4-carboxylic acid methyl ester (4.00 g) suspended in ethanol (150 mL) and ethyl acetate (150 mL) is added 5% palladium on carbon (0.300 g). The reaction mixture is placed under an atmosphere of hydrogen (50 psi) and shaken on a Parr apparatus. After 18 h, the reaction mixture is degassed with nitrogen and filtered though a plug of silica gel, eluting with 700 mL ethyl acetate and 600 mL methylene chloride. The filtrate is evaporated to give 2′-amino-4′-methoxy-biphenyl-4-carboxylic acid methyl ester (3.52 g, >99%) as a white solid.

Workup

  1. customthe reaction mixture is degassed with nitrogen
  2. filtrationfiltered though a plug of silica gel
  3. washeluting with 700 mL ethyl acetate and 600 mL methylene chloride
  4. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-53cb3b3332574665b469f0fedb26938c
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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