Ethanol → 4-Aminobenzene-1,3-dioic acid

HRID 1247177

Reaction equation

HRID 1247177 reaction equation
CCO.[N+:4]([C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[C:16]([OH:18])=[O:17])([O-])=O>[Pd].CC(O)=O>[NH2:4][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[C:16]([OH:18])=[O:17]

Participants

5

Reactant 2

HCID 702EthanolHCID 30624384-Nitroisophthalic acid

Product 1

HCID 113558524-Aminobenzene-1,3-dioic acidYield 75.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Into 20 mL EtOH and 20 mL HOAc was dissolved 2 g (9.48 mmol) 4-nitroisophthalic acid, and the solution was subjected to hydrogenation at atmospheric conditions over 1 g of 5% Pd on carbon. After 16 h, mixture was filtered, and filtrate was evaporated. The residue crystallized from methylene chloride-hexane, giving 1.29 g (75%) crystalline desired intermediate.

Workup

  1. filtrationmixture was filtered
  2. customfiltrate was evaporated
  3. customThe residue crystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-f1b9c8ee575c45eea6a0a0c2e1b6e831
Source dataset
uspto-grants-2006_10
Patent number
US07129245B2

Linked notes

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