6-Nitro-1,3-benzodioxole-5-carboxylic acid → 6-Amino-1,3-dioxaindane-5-carboxylic acid

HRID 1249742Notes

Reaction equation

HRID 1249742 reaction equation
[N+:1]([C:4]1[C:5]([C:13]([OH:15])=[O:14])=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[C:5]([C:13]([OH:15])=[O:14])=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1

Participants

4

Reactant 1

HCID 2464356-Nitro-1,3-benzodioxole-5-carboxylic acid

Product 1

HCID 70640686-Amino-1,3-dioxaindane-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6-nitro-benzo[1,3]dioxole-5-carboxylic acid (19 g, 90 mmol) in 500 mL ethanol was hydrogenated at 50 psig over 5 g of 5% palladium on carbon for 2 hours. Catalyst was filtered off with Celite® and solvent was removed in vacuo to give 6-amino-benzo[1,3]dioxole-5-carboxylic acid; 4.5 g (27%) used without further purification.

Workup

  1. filtrationCatalyst was filtered off with Celite® and solvent
  2. customwas removed in vacuo

Sources & evidence

ORD record
ord-da548b281880445a87ff4140c4ae6b43
Source dataset
uspto-grants-2002_01
Patent number
US06335344B1

Reaction notes

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