2-[(2-Chloro-6-nitrophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone → 2-[(6-Amino-2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone

HRID 2308900Notes

Reaction equation

HRID 2308900 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[CH2:11][N:12]1[C:16](=[O:17])[C:15]([CH3:19])([CH3:18])[CH2:14][O:13]1.[H][H]>C(O)C.[Pt]=O>[NH2:8][C:4]1[C:3]([CH2:11][N:12]2[C:16](=[O:17])[C:15]([CH3:18])([CH3:19])[CH2:14][O:13]2)=[C:2]([Cl:1])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 139349442-[(2-Chloro-6-nitrophenyl)methyl]-4,4-dimethyl-3-isoxazolidinoneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 139349452-[(6-Amino-2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinoneYield 59.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

Under an argon atmosphere, platinum oxide (0.3 g) was added to a Parr bottle (500 ml), followed by a solution of 2-[(2-chloro-6-nitrophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone (9.4 g, 0.033 mole) in ethanol (150 ml). The Parr bottle was placed on a Parr hydrogenation apparatus and charged with hydrogen. The reaction mixture was allowed to shake until the calculated amount of hydrogen was absorbed. The catalyst was removed by vacuum filtration. The filtrate was concentrated under reduced pressure to a residue. The residue was chromatographed on silica gel, eluting with 1:4 ethyl acetate:heptane. The appropriate fractions were combined and concentrated under reduced pressure to yield 5.0 g of 2-[(6-amino-2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone as a white solid.

Workup

  1. customwas absorbed
  2. customThe catalyst was removed by vacuum filtration
  3. concentrationThe filtrate was concentrated under reduced pressure to a residue
  4. customThe residue was chromatographed on silica gel
  5. washeluting with 1:4 ethyl acetate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6436e4a5ef6d43208283fc23f29d1e20
Source dataset
uspto-grants-1987_09
Patent number
US04692182

Reaction notes

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