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Ethyl(4-[2-methyl-2-nitropropyl]phenoxy)ethanoate → Ethyl(4-[2-amino-2-methylpropyl]phenoxy)ethanoate

HRID 2119819
Notes
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Reaction equation

HRID 2119819 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([CH3:19])([N+:16]([O-])=O)[CH3:15])=[CH:9][CH:8]=1)[CH3:2].[H][H]>C(O)C.[Pt]=O>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([NH2:16])([CH3:15])[CH3:19])=[CH:9][CH:8]=1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 22147737Ethyl(4-[2-methyl-2-nitropropyl]phenoxy)ethanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 22147764Ethyl(4-[2-amino-2-methylpropyl]phenoxy)ethanoateYield 28%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl(4-[2-methyl-2-nitropropyl]phenoxy)ethanoate (3.6 g, 12.8 mmol) in ethanol (35 mL) was charged with platinum oxide (0.72 g) and hydrogenated on a Parr shaker using 60 psi of hydrogen for 72 h at room temperature. The catalyst was filtered and the solution concentrated in vacuo. The resulting residue was purified by flash chromatography over silica gel eluting with 5% MeOH/CHCl3/NH3 to provide 0.9 g (28%) of a clear oil. MS (FD+): m/z 251.

Workup

  1. customfor 72 h
  2. customat room temperature
  3. filtrationThe catalyst was filtered
  4. concentrationthe solution concentrated in vacuo
  5. customThe resulting residue was purified by flash chromatography over silica gel eluting with 5% MeOH/CHCl3/NH3

Sources & evidence

ORD record
ord-2480686490e74ef9988805e582fde6c0
Source dataset
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06686372B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes