3-[(Tert-butoxy)carbonyl]-5-nitrobenzoic acid → 3-Amino-5-(tert-butoxycarbonyl)benzoic acid

HRID 562525Notes

Reaction equation

HRID 562525 reaction equation
[C:1]([O:5][C:6](=[O:19])[C:7]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[C:9]([C:10]([OH:12])=[O:11])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6](=[O:19])[C:7]1[CH:15]=[C:14]([NH2:16])[CH:13]=[C:9]([C:10]([OH:12])=[O:11])[CH:8]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 693810873-[(Tert-butoxy)carbonyl]-5-nitrobenzoic acid

Product 1

HCID 866192463-Amino-5-(tert-butoxycarbonyl)benzoic acidYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-Nitro-isophthalic acid mono t-Butyl ester (2.38 g, 8.9 mmol) was dissolved in EtOAc (50 ml). 10% Palladium on activated charcoal was added and the mixture was hydrogenated at 1 atm and room temperature. After 24 h, the mixture was filtered through a glass microfiber filter and the filtrate was concentrated to give the title compound as white crystals in 98% yield (2.07 g).

Workup

  1. customwas hydrogenated at 1 atm and room temperature
  2. filtrationthe mixture was filtered through a glass microfiber
  3. filtrationfilter
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6f7c1bd0e45f41589e2474486d6ee0f1
Source dataset
uspto-grants-2011_11
Patent number
US08067362B2

Reaction notes

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