Ethyl Acetate → tert-Butyl 4-amino-2-chlorobenzoate

HRID 1660868Notes

Reaction equation

HRID 1660868 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C(OCC)(=O)C>C(O)C.[Pt]>[NH2:15][C:13]1[CH:12]=[CH:11][C:3]([C:4]([O:6][C:7]([CH3:9])([CH3:10])[CH3:8])=[O:5])=[C:2]([Cl:1])[CH:14]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 22593093tert-Butyl 2-chloro-4-nitrobenzoate

Product 1

HCID 53432585tert-Butyl 4-amino-2-chlorobenzoateYield 96.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 2-chloro-4-nitro-benzoate (2.05 g, 7.98 mmol) in ethanol 12 mL) and ethyl acetate (108 mL) was added platinum on activated charcoal (5%, 295 mg), and the mixture was stirred under at room temperature under a hydrogen atmosphere (1 bar). After filtration through a pad of diatomaceous earth, the filtrate was evaporated to afford tert-butyl 4-amino-2-chlorobenzoate (1.75 g, 96%). Orange solid, MS (EI)=227.2 (M+).

Workup

  1. filtrationAfter filtration through a pad of diatomaceous earth
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-025b808d1d654df096813c1b798ab662
Source dataset
uspto-grants-2011_10
Patent number
US08030308B2

Reaction notes

Loading…