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

HRID 42539

Reaktionsgleichung

Reaktionsgleichung von HRID 42539
[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]>CO.[OH-].[OH-].[Pd+2]>[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]

Komponenten

4

Edukt 1

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

Produkt 1

HCID 135576433-Amino-5-(methoxycarbonyl)benzoic acidAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

20% Pd(OH)2 (0.50 g) was carefully wetted down under argon with methanol (5 mL) and then 3-(methoxycarbonyl)-5-nitrobenzoic acid (5.00 g, 22.2 mmol) in methanol (20 mL) was added. The mixture was then hydrogenated on a Parr Shaker apparatus for 5 hours at 50 psi. Under argon, the reaction was carefully filtered through a fiberglass filter paper. The filtrate was concentrated to give 3-amino-5-(methoxycarbonyl)benzoic acid (4.0 g, 20.5 mmol, 92% yield) of off-white solids as product. MS found: (M−H)+=194.

Aufarbeitung

  1. filtrationUnder argon, the reaction was carefully filtered through a fiberglass
  2. filtrationfilter paper
  3. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-1ee157a6663846bc9fb7d0b8b6770e51
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536198B2

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