2-(tert-butyl-dimethyl-silanyloxy)-5-Nitrobenzoic acid methyl ester → 5-Amino-2-(tert-butyl-dimethyl-silanyloxy)benzoic acid methyl ester

HRID 884432Notes

Reaction equation

HRID 884432 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].[H][H]>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[O:13][Si:14]([C:17]([CH3:19])([CH3:18])[CH3:20])([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 692965332-(tert-butyl-dimethyl-silanyloxy)-5-Nitrobenzoic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 692965665-Amino-2-(tert-butyl-dimethyl-silanyloxy)benzoic acid methyl esterYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(tert-butyl-dimethyl-silanyloxy)-5-Nitrobenzoic acid methyl ester (4.9 g, 16 mmol) in ethanol (100 mL) was treated with hydrogen gas (60 psi) for 48 h in the presence of palladium on carbon catalyst (0.31 g, 10% Pd). The catalyst was removed by filtration through CELITE®, and the filtrate was concentrated to a syrup and dried in vacuo to afford the intermediate 5-amino-2-(tert-butyl-dimethyl-silanyloxy)-benzoic acid methyl ester as a dark brown solid (4.52 g, 99%).

Workup

  1. customThe catalyst was removed by filtration through CELITE®
  2. concentrationthe filtrate was concentrated to a syrup
  3. customdried in vacuo

Sources & evidence

ORD record
ord-7d5dc3c2c4ec4d7d8ae4d4ef26dcfc20
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

Loading…