Methyl 3-(3-nitrophenyl)benzoate → (1,1'-Biphenyl)-3-carboxylic acid, 3'-amino-, methyl ester

HRID 399849Notes

Reaction equation

HRID 399849 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH:7]=[CH:8][CH:9]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 11708671Methyl 3-(3-nitrophenyl)benzoate

Product 1

HCID 1394215(1,1'-Biphenyl)-3-carboxylic acid, 3'-amino-, methyl esterYield 82.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (0.4 g) was added to a solution of methyl 3-(3-nitrophenyl)benzoate (2.0 g) in methanol (30 ml) and the mixture was subjected to catalytic hydrogenation at ambient temperature under atmospheric pressure. After one hour, the catalyst was removed by filtration and the filtrate was evaporated in vacuo. The residue was crystallized from diethyl ether to afford methyl 3-(3-aminophenyl)benzoate (1.45 g).

Workup

  1. customwas subjected to catalytic hydrogenation at ambient temperature under atmospheric pressure
  2. customthe catalyst was removed by filtration
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-444cb609207f42e2bbc4f0a704d24025
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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