8-(2,5-Dimethyl-4-nitrophenyl)-1,4-dioxaspiro[4.5]dec-7-ene → 2,5-Dimethyl-4-(1,4-dioxaspiro[4.5]decan-8-yl)aniline

HRID 2093808Notes

Reaction equation

HRID 2093808 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([CH3:11])=[CH:4][C:3]=1[C:12]1[CH2:21][CH2:20][C:15]2([O:19][CH2:18][CH2:17][O:16]2)[CH2:14][CH:13]=1>CCO.[Pd]>[CH3:11][C:5]1[CH:4]=[C:3]([CH:12]2[CH2:21][CH2:20][C:15]3([O:19][CH2:18][CH2:17][O:16]3)[CH2:14][CH2:13]2)[C:2]([CH3:1])=[CH:7][C:6]=1[NH2:8]

Participants

4

Reactant 1

HCID 582571358-(2,5-Dimethyl-4-nitrophenyl)-1,4-dioxaspiro[4.5]dec-7-ene

Product 1

HCID 582571202,5-Dimethyl-4-(1,4-dioxaspiro[4.5]decan-8-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 8-(2,5-Dimethyl-4-nitrophenyl)-1,4-dioxaspiro[4.5]dec-7-ene (105 mg, 0.36 mmol) and Pd/C (10 mg) in EtOH was degassed and stirred under 1 atm. H2 at room temperature for 14 h. Pd/C was removed by filtration and filtrate was concentrated to provide 2,5-dimethyl-4-(1,4-dioxaspiro[4.5]decan-8-yl)aniline, which was used in the next step without further purification; ESMS m/z 262.2 (M+H+).

Workup

  1. customwas degassed
  2. customPd/C was removed by filtration and filtrate
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-3342f016ea67438990a84bf3c75291ca
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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