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

HRID 1987731Notes

Reaction equation

HRID 1987731 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) beta 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-e226cd9b67ae42e3b87c85d77f2410dc
Source dataset
uspto-grants-2009_06
Patent number
US07553831B2

Reaction notes

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