2-(4-Methoxy-phenoxy)-5-nitro-benzoic acid methyl ester → HCID 54346018, compound

HRID 47438Notes

Reaction equation

HRID 47438 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 540755342-(4-Methoxy-phenoxy)-5-nitro-benzoic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 54346018HCID 54346018, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The compound of step 1 (2.3 g) in methanol (150 ml) containing 10% Pd/C (0.5 g) was hydrogenated under one atmosphere of hydrogen for 18 h. The mixture was filtered (kieselguhr) and solvent removed from the filtrate under reduced pressure to give the title compound (2.0 g) as a yellow oil. 1H NMR (CDCl3) δ: 3.69 (2H, brs), 3.77 (6H, s), 6.76-6.87 (6H, m), 7.19 (1H, d, J=2.5 Hz).

Workup

  1. filtrationThe mixture was filtered (kieselguhr) and solvent
  2. customremoved from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-aaf8ecbfeabc41609627124b2c8edee2
Source dataset
uspto-grants-2004_03
Patent number
US06699879B1

Reaction notes

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