t-Butyl 3-methyl-4-nitrophenoxyacetate → Tert-butyl 2-(4-amino-3-methylphenoxy)acetate

HRID 1592028Notes

Reaction equation

HRID 1592028 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([CH3:18])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6](=[O:19])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([CH3:18])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 23370041t-Butyl 3-methyl-4-nitrophenoxyacetate

Product 1

HCID 23370016Tert-butyl 2-(4-amino-3-methylphenoxy)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2.35 g (8.8 mmol) of the title A compound, (3-methyl-4-nitrophenoxy)-acetic acid t-butyl ester in 40 mL of EtOH is hydrogenated at 45 psi for 18 h in the presence of 10% Pd/C. The catalyst is removed by filtration through Celite and the filtrate is concentrated to give (4-amino-3-methylphenoxy)-acetic acid t-butyl ester as an oil: 1H-NMR (CDCl3) δ 6.68 (br s, 1H), 6.61 (s, 2H), 4.43 (s, 2H), 2.15 (s, 3H), 1.48 (s, 9H); [M+1]+=238.

Workup

  1. customThe catalyst is removed by filtration through Celite
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-c2dd2e9f682e4247ad386cafecf9d55a
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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