7-Nitrobenzo[d][1,3]dioxole-4-carboxylic acid → 7-Amino-1,3-dioxaindane-4-carboxylic acid

HRID 2055019Notes

Reaction equation

HRID 2055019 reaction equation
[N+:1]([C:4]1[C:9]2[O:10][CH2:11][O:12][C:8]=2[C:7]([C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[C:9]2[O:10][CH2:11][O:12][C:8]=2[C:7]([C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 219488047-Nitrobenzo[d][1,3]dioxole-4-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 219488227-Amino-1,3-dioxaindane-4-carboxylic acidYield 98.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

8.05 g of 7-nitro-benzo[1,3]dioxole-4-carboxylic acid is reacted with hydrogen in 650 ml of ethanol with 800 mg of palladium/carbon catalyst under normal pressure at room temperature. It is filtered through diatomaceous earth and concentrated by evaporation in a vacuum. 6.82 g of 7-amino-benzo[1,3]dioxole-4-carboxylic acid is obtained as a brown solid, flash point 196-197° C.

Workup

  1. filtrationIt is filtered through diatomaceous earth
  2. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-1c81d56428284659b175840058fee591
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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