HCID 121386223, compound → HCID 89691048, compound

HRID 2202855Notes

Reaction equation

HRID 2202855 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-])=O)=[C:6]([N:8]([CH3:16])[C:9](=O)[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:7]=1>CC(O)=O.[Zn]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:17]=[C:9]([CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[N:8]([CH3:16])[C:6]=2[CH:7]=1

Participants

4

Reactant 1

HCID 121386223HCID 121386223, compound

Product 1

HCID 89691048HCID 89691048, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of N-(5-bromo-2-nitrophenyl)-N,3,3-trimethylbutanamide (300 mg) in AcOH (5 ml) was added zinc (596 mg) at room temperature. Then the mixture was heated at 90° C. for 2 h. The inorganic material was removed by filtration, and the filtrate was concentrated. The residue was poured into a mixture of EtOAc and saturated NaHCO3 solution. The organic layer was washed with brine, dried over MgSO4, concentrated, and purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (200 mg) as a white solid.

Workup

  1. customThe inorganic material was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. additionThe residue was poured into a mixture of EtOAc and saturated NaHCO3 solution
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. custompurified by NH silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-87600820f9ff4ea9aebb142106662190
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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