Stannous chloride dihydrate → HCID 68466877, compound

HRID 1945179Notes

Reaction equation

HRID 1945179 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[O:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([N+:15]([O-])=O)=[C:10]([Cl:18])[CH:9]=1)([CH3:3])[CH3:2].O.O.[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>O1CCOCC1.Cl>[CH:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[O:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([NH2:15])=[C:10]([Cl:18])[CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 68467890HCID 68467890, compound

Product 1

HCID 68466877HCID 68466877, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3.80 g (12.5 mmol) of 4-(3-isopropylphenoxy)-2-chloro-5-methylnitrobenzene in 60 ml of dioxane and 60 ml of hydrochloric acid is admixed with 8.41 g (37.2 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 NaHCO3 and extracted repeatedly with dichloromethane, and the extracts are dried over Na2SO4 and filtered, and the solvent is removed under reduced pressure (3.47 g, 94.5% purity, 95.7% yield, log P (pH 2.3)=4.68).

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 (3.47 g, 94.5% purity, 95.7% yield, log P (pH 2.3)=4.68)

Sources & evidence

ORD record
ord-3e10f36be9ab44139998c04f94540d0d
Source dataset
uspto-grants-2013_03
Patent number
US08394991B2

Reaction notes

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