Stannous chloride dihydrate → (3-Amino-4-methylphenoxy) acetonitrile

HRID 1106715Notes

Reaction equation

HRID 1106715 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][C:8]#[N:9])=[CH:4][C:3]=1[N+:12]([O-])=O.O.O.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[CH3:1])[O:6][CH2:7][C:8]#[N:9]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 18789631(4-Methyl-3-nitrophenoxy) acetonitrile

Product 1

HCID 18789626(3-Amino-4-methylphenoxy) acetonitrileYield 53.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

(4-Methyl-3-nitrophenoxy)-acetonitrile (6.0 g) was dissolved in 120 ml of ethyl acetate and treated with 21.8 g of tin (II) chloride dihydrate; and the mixture was stirred at 70° C. for 2 hours. The mixture was cooled, poured into a saturated solution of sodium bicarbonate, extracted with ethyl acetate, dried, and evaporated. The residue was purified by silica gel chromatography eluting with ethyl acetate:hexane (7:3) to give 2.7 g of (3-amino-4-methylphenoxy)-acetonitrile. ##STR75##

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. customdried
  4. customevaporated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with ethyl acetate:hexane (7:3)

Sources & evidence

ORD record
ord-a30f6d0c5d1d4d4e86f6d4c076baa654
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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