1,3-Benzenedicarboxylic acid, 5-nitro-, 1-methyl ester → 3-Amino-5-(methoxycarbonyl)benzoic acid

HRID 1454183Notes

Reaction equation

HRID 1454183 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([N+:14]([O-])=O)[CH:13]=1)[C:8]([OH:10])=[O:9])=[O:4]>[Pd].CO>[NH2:14][C:12]1[CH:11]=[C:7]([CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:13]=1)[C:8]([OH:10])=[O:9]

Participants

4

Reactant 1

HCID 747761,3-Benzenedicarboxylic acid, 5-nitro-, 1-methyl ester

Product 1

HCID 135576433-Amino-5-(methoxycarbonyl)benzoic acidYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 3-(methoxycarbonyl)-5-nitrobenzoic acid (11.25 g, 50 mmol) and palladium on carbon (10 wt %, 1.0 g) in MeOH (10 mL) was shaken in hydrogenator under hydrogen at 50 psi for 3 h. The mixture was filtered and concentrated in vacuo to give the title compound (8.0 g, 82% yield): 1H NMR (CD3OD, 500 MHz) δ ppm 3.91 (3H, s), 7.53 (1H, m), 7.55 (1H, m), 7.92 (1H, m). HPLC retention time: 0.922 min (method A). MS (ESI) (M+H)+ 196.12.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-496b680215d346dc8f9d76865e627322
Source dataset
uspto-grants-2009_01
Patent number
US07476764B2

Reaction notes

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