Tert-butyl 2-nitrobenzoate → tert-Butyl 2-aminobenzoate

HRID 2289801Notes

Reaction equation

HRID 2289801 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([O-])=O>CCO.[C].[Pd]>[NH2:1][C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

4

Reactant 1

HCID 4860715Tert-butyl 2-nitrobenzoate

Product 1

HCID 3430448tert-Butyl 2-aminobenzoateYield 94.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of t-butyl 2-nitrobenzoate (4.9 g, 22 mmol) in EtOH (160 mL) was stirred with 10% palladium-carbon (700 mg) under an atmosphere of H2 (60 psi) at 23° C. After 4 h, the mixture was filtered and evaporated in vacuo to give t-butyl 2-aminobenzoate (4.0 g, 20.7 mmol) as a yellow oil.

Workup

  1. filtrationthe mixture was filtered
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-2270727849f141ceb86fdb5806a49b07
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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