Tert-butyl 2-ethoxy-4-nitrobenzoate → Tert-butyl 4-amino-2-ethoxybenzoate

HRID 714853Notes

Reaction equation

HRID 714853 reaction equation
[CH2:1]([O:3][C:4]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:5]=1[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH3:2]>C(O)C.[C].[Pd]>[NH2:17][C:15]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:11])([CH3:12])[CH3:10])=[O:7])=[C:4]([O:3][CH2:1][CH3:2])[CH:16]=1

Participants

4

Reactant 1

HCID 117840120Tert-butyl 2-ethoxy-4-nitrobenzoate

Product 1

HCID 117840502Tert-butyl 4-amino-2-ethoxybenzoateYield 96.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 2-ethoxy-4-nitrobenzoate (550 mg) obtained in Step B of Example 139 in ethanol (10 mL) was added 10% palladium-carbon (42 mg), and the mixture was stirred overnight at room temperature under hydrogen atmosphere (at normal pressures). The palladium carbon was removed by filtration through Celite, and the solvent was evaporated under reduced pressure to give the title compound (470 mg).

Workup

  1. customThe palladium carbon was removed by filtration through Celite
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c2d8f2802bff48359dfa6b9f58b63d50
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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