Tert-butyl 4-hydroxy-3-nitrobenzoate → tert-Butyl 3-amino-4-hydroxybenzoate

HRID 1007142Notes

Reaction equation

HRID 1007142 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][C:3]=1[N+:15]([O-])=O>CO.[Pd]>[OH:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:11])([CH3:12])[CH3:10])=[O:7])=[CH:4][C:3]=1[NH2:15]

Participants

4

Reactant 1

HCID 22667857Tert-butyl 4-hydroxy-3-nitrobenzoate

Product 1

HCID 11160103tert-Butyl 3-amino-4-hydroxybenzoateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-hydroxy-3-nitrobenzoate (4.4 g, 18.4 mmol) in methanol (50 mL), 10% Pd/C (200 mg) was added and the resulting suspension was hydrogenated at 50 psi for 4 hours. After filtering under a pad of celite, methanol was removed in vacuo to obtain the title compound as a greenish powder (3.5 g, 95%).

Workup

  1. filtrationAfter filtering under a pad of celite, methanol
  2. customwas removed in vacuo

Sources & evidence

ORD record
ord-fc2cbcda67684e34a63a41f1d2f1d8bd
Source dataset
uspto-grants-2004_09
Patent number
US06794385B2

Reaction notes

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