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

HRID 1599099Notes

Reaction equation

HRID 1599099 reaction equation
[C:1]([O:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 11961369Tert-butyl 3-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 2737408tert-Butyl-3-aminobenzoateYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-nitro-benzoic acid t-butyl ester (3.77 g, 16.9 mmol) in absolute ethanol (50 mL) was combined with palladium on carbon (10 wt %, 0.30 g) and hydrogenated under a baloon of hydrogen gas for appoximately 3 hrs. The reaction mixture was filtered through a pad of diatomaceous earth and then concentrated in vacuo to an oil which crystallized when dried under high vacuum providing 3.28 g of the title compound as a tan solid. 1H NMR (300 MHz, CDCl3) d 7.38 (d, 1H, J=8.0 Hz), 7.29 (m, 1H), 7.19 (m, 1H), 6.83 (m, 1H), 1.58 (s, 9H); low resolution MS (Cl) m/e 194 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  2. concentrationconcentrated in vacuo to an oil which
  3. customcrystallized when
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-bead67553bb640ea9268daaa1889929f
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

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