Monomethyl-5-nitroisophthalate → 3-Amino-5-(methoxycarbonyl)benzoic acid

HRID 348787

Reaction equation

HRID 348787 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([O-:16])=[O:15])[CH:7]=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:5]=[C:6]([CH:7]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[CH:13]=1)[C:14]([OH:16])=[O:15]

Participants

4

Reactant 1

HCID 6931682Monomethyl-5-nitroisophthalate

Product 1

HCID 135576433-Amino-5-(methoxycarbonyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of mono-methyl 5-nitro-isophthalate (22.5 g, 100 mmol) and palladium on carbon (5%, 2.00 g) in methanol (100 mL) is shaken in a hydrogenation apparatus under hydrogen (50 psi) for 3 hours. The mixture is then filtered through diatomaceous earth and concentrated to give the title compound, NMR (300 MHz, CDCl3) delta 7.67, 7.41, 7.40 and 3.83; MS (ESI—) for C9H9NO4 m/z (M−H)−=194.

Workup

  1. filtrationThe mixture is then filtered through diatomaceous earth
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-23aa14780da64a0580a587d752837938
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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