Methanol → Ethyl 3-amino-4-(2-isopropyl-1H imidazol-1-yl)benzoate

HRID 2068968Notes

Reaction equation

HRID 2068968 reaction equation
[CH:1]([C:4]1[N:5]([C:9]2[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10]=2[N+:20]([O-])=O)[CH:6]=[CH:7][N:8]=1)([CH3:3])[CH3:2].CO>[H][H].[C].[Pd]>[NH2:20][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][C:9]=1[N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[CH:1]([CH3:2])[CH3:3])[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 2

HCID 887MethanolHCID 59198553Ethyl 4-(2-isopropyl-1H-imidazol-1-yl)-3-nitrobenzoate

Product 1

HCID 59198643Ethyl 3-amino-4-(2-isopropyl-1H imidazol-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of ethyl 4-(2-isopropyl-1H-imidazol-1-yl)-3-nitrobenzoate as synthesized in above Production Example 9, 4.94 g, methanol 150 mL and 10% palladium carbon 500 mg was stirred for 16 hours in hydrogen atmosphere. After removing the insoluble matter by filtration, the solvent was distilled off to provide 4.12 g of the title compound.

Workup

  1. customAfter removing the insoluble matter
  2. filtrationby filtration
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-e6062c18a3c849cc9382ab27a4d9b45e
Source dataset
uspto-grants-2012_10
Patent number
US08299080B2

Reaction notes

Loading…