Tert-butyl 3-nitrobenzoate → tert-Butyl-3-aminobenzoate

HRID 2289803Notes

Reaction equation

HRID 2289803 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])([O-])=O>CCO.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[C:7]([O:9][C:10]([CH3:12])([CH3:13])[CH3:11])=[O:8]

Participants

4

Reactant 1

HCID 11961369Tert-butyl 3-nitrobenzoate

Product 1

HCID 2737408tert-Butyl-3-aminobenzoateYield 79.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

1H (CDCl3, 400 MHz) δ 1.4 (9H, s), 7.6 (1H, dd), 8.3 (1H, d), 8.4 (1H, d), 8.8 (1H, s) ppm. A solution of t-butyl 3-nitrobenzoate (5.8 g, 26 mmol) in EtOH (260 mL) was stirred with 10% palladium-carbon (1.0 g) 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 3-aminobenzoate (4.0 g, 20.7 mmol) as a white solid.

Workup

  1. filtrationthe mixture was filtered
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-465a378ca5e14bd79a6276e4129c0da4
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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