HCID 21699153, compound → HCID 22461667, compound

HRID 1597176Notes

Reaction equation

HRID 1597176 reaction equation
[C:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=1)([OH:3])=[O:2]>CO.[Pd]>[C:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=1)([OH:3])=[O:2]

Participants

4

Reactant 1

HCID 21699153HCID 21699153, compound

Product 1

HCID 22461667HCID 22461667, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-carboxymethyl-5-methoxy-phenyl-oxy-(3-nitrobenzene) (57 g, 0.187 mol) and 10% Pd/C (11 g) was hydrogenated in MeOH (1000 mL) at 50 psi for 2 h. The solution was filtered through Celite® and the filtrate was concentrated. Flash chromatography (silica gel, 20% EtOAc/Hexane) yielded the title compound (49.3 g, 96%): MS (ES) m/e 274.1 (M+H)+.

Workup

  1. filtrationThe solution was filtered through Celite®
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-430d2745c17140988b0d18fe68961aa3
Source dataset
uspto-grants-2001_09
Patent number
US06294531B1

Reaction notes

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