HCID 21073088, compound → HCID 21073087, compound

HRID 1373256Notes

Reaction equation

HRID 1373256 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=2[N+:25]([O-])=O)[CH:12]=1)([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2]>[C].[Pd].C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=2[NH2:25])[CH:12]=1)([CH3:10])[CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 21073088HCID 21073088, compound

Product 1

HCID 21073087HCID 21073087, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5% carbon-palladium (1.0 g) was added to an ethyl acetate (100 ml) solution of tert-butyl[1-[3-(5-chloro-2-nitrophenoxy)phenyl]-1-methylethyl]carbamate (3.3 g, 8.1 mmols). The resulting mixture was hydrogenated at room temperature under atmospheric pressure for 3 hours. The catalyst was removed through filtration, and the filtrate was concentrated under reduced pressure. The residue was purified through silica gel column chromatography to give an amorphous solid of tert-butyl[1-[3-(2-amino-5-chlorophenoxy)phenyl]-1-methylethyl]carbamate (2.7 g, 89%).

Workup

  1. customThe catalyst was removed through filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-6414d22ae285415e87765933b2f2ee2a
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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