Stannous chloride dihydrate → HCID 18789695, compound

HRID 1106736Notes

Reaction equation

HRID 1106736 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:12]([O-])=O)[CH:11]=1)[O:5][CH2:6][C:7]#[N:8].O.O.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:11]=1)[O:5][CH2:6][C:7]#[N:8]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 18789745HCID 18789745, compound

Product 1

HCID 18789695HCID 18789695, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
70 °C

Procedure

A warm solution of 8.23 g of (3-chloro-5-nitro-phenoxy)-acetonitrile in 150 ml of ethyl acetate was treated with 34.9 g of tin (II) chloride dihydrate and the solution was heated at 70° C. for 2 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, basified with saturated sodium bicarbonate solution, extracted twice with ethyl acetate, dried (MgSO4), and evaporated to dryness. The residue was purified by silica gel chromatography using ethyl acetate/hexane (35:65) as solvent and obtained 4.42 g of (3-amino-5-chloro-phenoxy)-acetonitrile as a cream solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted twice with ethyl acetate
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ba8985e222a04837877d388ad7e890e3
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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