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

HRID 2164681Notes

Reaction equation

HRID 2164681 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>CO.[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 887.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 2-nitrobenzoate (2.1 g.) in methanol (200 ml.) was hydrogenated over palladium-carbon (2 g.) with shaking at atmospheric pressure and room temperature for 3.5 hours. The reaction mixture was filtered to remove the catalyst and then evaporated. To the residue were successively added diethyl ether and an aqueous solution of sodium chloride followed by shaking. The organic layer was separated, dried over magnesium sulfate, treated with activated charcoal and then evaporated to give an oil of the title compound (16.13 g.).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. customevaporated
  4. stirringby shaking
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. additiontreated with activated charcoal
  8. customevaporated

Sources & evidence

ORD record
ord-6574e45b1c90479882da78f4532fb22a
Source dataset
uspto-grants-1985_03
Patent number
US04506076

Reaction notes

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