HCID 10356009, compound → 2-Hydroxy-4-(4-amino-phenoxy)-benzoic acid

HRID 18445Notes

Reaction equation

HRID 18445 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]>CCO.C1COCC1.[Pd]>[OH:1][C:2]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 1

HCID 10356009HCID 10356009, compound

Product 1

HCID 104670322-Hydroxy-4-(4-amino-phenoxy)-benzoic acidYield 35%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A slurry of 2-hydroxy-4-(4-nitro-phenoxy)benzoic acid (950 mg; 3.5 mmol) in 99% EtOH (30 mL) and THF (0.5 mL) was added 5% Pd/C (100 mg) and stirred under H2 atmosphere (1 atm.) for 25 minutes. The black solution was filtered through celite and evaporated to dryness yielding 300 mg (35%) of a brown powder. Mp. 187-188° C.; MS (ESI+): 246 (MH+).

Workup

  1. filtrationThe black solution was filtered through celite
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-d41b52a57aae469f902a4b7e6e561cc4
Source dataset
uspto-grants-2010_06
Patent number
US07741352B2

Reaction notes

Loading…