Stannous chloride dihydrate → HCID 18319266, compound

HRID 1701003Notes

Reaction equation

HRID 1701003 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=2[CH3:18])[CH:6]=[CH:7][CH:8]=1)#[N:2].O.O.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=2)=[C:10]([CH3:18])[CH:11]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 18319281HCID 18319281, compound

Product 1

HCID 18319266HCID 18319266, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

1-(3-Cyanophenyl)-2-methyl-4-nitrobenzene (3.0 gm, 12.61 mmol) and tin(II) chloride dihydrate were suspended in ethanol (30 mL) and heated to 70° C. for 30 mins. After being cooled, the mixture was poured onto ice, and neutralised by the addition of sodium bicarbonate. The mixture was then extracted with dichloromethane (3×50 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to give 4-amino-1-(3-cyanophenyl)-2-methylbenzene (1.8 gm, 69%) as a yellow oil.

Workup

  1. temperatureAfter being cooled
  2. additionthe mixture was poured onto ice
  3. extractionThe mixture was then extracted with dichloromethane (3×50 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c3ae18d631b24ac3bd1b53aef9b4b289
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

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