Stannous chloride dihydrate → 4-(4-Cyclohexylphenoxy)-2,5-dimethylaniline

HRID 405004

Reaction equation

HRID 405004 reaction equation
[CH:1]1([C:7]2[CH:24]=[CH:23][C:10]([O:11][C:12]3[C:17]([CH3:18])=[CH:16][C:15]([N+:19]([O-])=O)=[C:14]([CH3:22])[CH:13]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.O.[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>O1CCOCC1.Cl>[CH:1]1([C:7]2[CH:24]=[CH:23][C:10]([O:11][C:12]3[C:17]([CH3:18])=[CH:16][C:15]([NH2:19])=[C:14]([CH3:22])[CH:13]=3)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 685962084-(4-Cyclohexylphenoxy)-2,5-dimethylnitrobenzene

Product 1

HCID 685960764-(4-Cyclohexylphenoxy)-2,5-dimethylanilineYield 61.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.49 g (1.5 mmol) of 4-(4-cyclohexylphenoxy)-2,5-dimethylnitrobenzene in 7 ml of dioxane and 7 ml of hydrochloric acid is admixed with 1.01 g (4.5 mmol) of tin(II) chloride dihydrate at room temperature and the mixture is then refluxed for 2 h. It is cooled to room temperature, neutralized with aqueous NaHCO3 and extracted repeatedly with dichloromethane, and the extracts are dried over Na2SO4 and filtered, and the solvent is removed under reduced pressure. This is followed by purification by column chromatography (0.29 g, purity 95.2%, yield 61.5%, log P (pH 2.3)=4.25).

Workup

  1. temperaturethe mixture is then refluxed for 2 h
  2. extractionextracted repeatedly with dichloromethane
  3. dry with materialthe extracts are dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent is removed under reduced pressure
  6. customThis is followed by purification by column chromatography (0.29 g, purity 95.2%, yield 61.5%, log P (pH 2.3)=4.25)

Sources & evidence

ORD record
ord-018238e3bc1740f199fda69cbcf3f27c
Source dataset
uspto-grants-2014_06
Patent number
US08748662B2

Linked notes

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