Tin tetrachloride → HCID 13827858, compound

HRID 2182398Notes

Reaction equation

HRID 2182398 reaction equation
[CH2:1]([C:3]1[C:9]([CH3:10])=[CH:8][C:6]([NH2:7])=[C:5]([N+:11]([O-])=O)[CH:4]=1)[CH3:2].[Sn](Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>CO>[CH2:1]([C:3]1[C:9]([CH3:10])=[CH:8][C:6]([NH2:7])=[C:5]([NH2:11])[CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 22477886HCID 22477886, compound

Product 1

HCID 13827858HCID 13827858, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 4-ethyl-5-methyl-2-nitro-aniline [484 mg, Reference Example 31(b)] in methanol (20 ml) was treated with tin chloride (5.09 g), then heated at reflux for 16 hours and then cooled to ambient temperature. The pH of the reaction mixture was adjusted to pH 8 by addition of aqueous sodium bicarbonate and then this mixture was extracted with ethyl acetate. The organic extracts were dried over magnesium sulfate and then evaporated to give 4-ethyl-5-methyl-phenylene diamine (374 mg) as an off-white solid. LC-MS (METHOD B): RT=1.80 minutes; 151.25 (M+H)+. (b) 4-Isopropyl-5-methyl-phenylene diamine

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hours
  3. extractionthis mixture was extracted with ethyl acetate
  4. dry with materialThe organic extracts were dried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-d6d9f2d1d50640ee932ebcd6c3a3965f
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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