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

HRID 2093791Notes

Reaction equation

HRID 2093791 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([CH3:11])=[CH:4][C:3]=1[CH:12]1[CH2:21][CH2:20][C:15]2([O:19][CH2:18][CH2:17][O:16]2)[CH2:14][CH2:13]1>CO.[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 671675958-(2,5-Dimethyl-4-nitrophenyl)-1,4-dioxaspiro[4.5]decane

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 8-(2,5-dimethyl-4-nitrophenyl)-1,4-dioxaspiro[4.5]decane (130.2 mg, 0.45 mmol) and 10% Pd—C (13.0 mg) in MeOH (20 mL) was degassed and then reacted under 1 atm. H2. Upon reaction completion, the Pd—C was removed by filtration and the filtrate was concentrated in vacuo to afford 2,5-dimethyl-4-(1,4-dioxaspiro[4.5]decan-8-yl)aniline; ESMS m/z 262.2 (M+H+).

Workup

  1. customwas degassed
  2. customreacted under 1 atm
  3. customUpon reaction completion
  4. customthe Pd—C was removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e43fc6f270844014aa2f0a38076dcd2c
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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