HCID 68859786, compound → Methyl 2-[(4′-amino[1,1′-biphenyl]-4-yl)oxy]acetate

HRID 493514Notes

Reaction equation

HRID 493514 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1>[Pd].CO>[CH3:1][O:2][C:3](=[O:21])[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 68859786HCID 68859786, compound

Product 1

HCID 68860613Methyl 2-[(4′-amino[1,1′-biphenyl]-4-yl)oxy]acetateYield 34.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (4′-nitro-biphenyl-4-yloxy)-acetic acid methyl ester (2.26 g, 7.86 mmol), prepared in the previous step, and 10% palladium on carbon in methanol was hydrogenated under a hydrogen atmosphere at room temperature. The reaction was filtered and the filtrate concentrated under reduced pressure. Purification of the residue on silica gel using 20% ethyl acetate hexanes as the eluent gave (4′-amino-biphenyl-4-yloxy)-acetic acid methyl ester (700 mg. 31%).

Workup

  1. customwas hydrogenated under a hydrogen atmosphere at room temperature
  2. filtrationThe reaction was filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customPurification of the residue on silica gel using 20% ethyl acetate hexanes as the eluent

Sources & evidence

ORD record
ord-b80309e79e8b44d8aedfe257a663bb9b
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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