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

HRID 480670

Reaction equation

HRID 480670 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>C1COCC1.[Pd]>[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 8028TetrahydrofuranSolvent

Procedure

To 2.75 g of mono-methyl 5-nitroisophthalate (5-(methoxycarbonyl)-3-nitrobenzoic acid), compound 67, dissolved in 30 mL of THF was added 100 mg of 10% palladium on carbon. The reaction was placed in a Parr hydrogenator under a H2 atmosphere of 45 psi and shaken for 16 hr. The solid palladium catalyst was removed by vacuum filtration through celite and 5 mL of 1N HCl in diethyl ether was added to the filtrate. After sitting for 12 hr, the solid was collected by vacuum filtration and was washed with ethyl acetate. This provided 1.82 g of the desired product. The product was identified by 1H NMR and mass spectroscopy and purity was assessed by RP-HPLC.

Workup

  1. customThe solid palladium catalyst was removed by vacuum filtration through celite and 5 mL of 1N HCl in diethyl ether
  2. additionwas added to the filtrate
  3. waitAfter sitting for 12 hr
  4. filtrationthe solid was collected by vacuum filtration
  5. washwas washed with ethyl acetate

Sources & evidence

ORD record
ord-a83ddcf2e0354fd7ac022d81a00c447c
Source dataset
uspto-grants-2003_11
Patent number
US06653321B1

Linked notes

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