Tin tetrachloride → 5-Amino-3-chloropyridine-2-carbonitrile

HRID 1454488Notes

Reaction equation

HRID 1454488 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[Cl:6][C:7]1[C:8]([C:16]#[N:17])=[N:9][CH:10]=[C:11]([N+:13]([O-])=O)[CH:12]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:13][C:11]1[CH:12]=[C:7]([Cl:6])[C:8]([C:16]#[N:17])=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 218754953-Chloro-5-nitropicolinonitrile

Product 1

HCID 218750995-Amino-3-chloropyridine-2-carbonitrileYield 50.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of tin chloride (52 g) and 3-chloro-2-cyano-5-nitro-pyridine (10.3 g) was stirred in ethyl acetate (200 mL) at room temperature for 10 minutes and at 70° C. for 4 hours. The solution was cooled to room temperature and diluted with ethyl acetate (500 mL). Sodium bicarbonate (100 g) added in four portions to the mixture within 4 hours. The mixture was stirred vigorously for 20 hours. The suspension was filtered and the filtrate was washed with saturated aqueous sodium bicarbonate solution. The solvent was evaporated to give 5-amino-3-chloro-2-cyanopyridine (4.34 g) as an off-white powder.

Workup

  1. filtrationThe suspension was filtered
  2. washthe filtrate was washed with saturated aqueous sodium bicarbonate solution
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ce47b2270f794557b24b6a73f0b98c57
Source dataset
uspto-grants-2009_01
Patent number
US07479502B2

Reaction notes

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