Stannous chloride dihydrate → 5-Amino-3-(trifluoromethyl)pyridine-2-acetonitrile

HRID 576216Notes

Reaction equation

HRID 576216 reaction equation
O.O.[Sn](Cl)Cl.[N+:6]([C:9]1[CH:10]=[C:11]([C:18]([F:21])([F:20])[F:19])[C:12]([CH2:15][C:16]#[N:17])=[N:13][CH:14]=1)([O-])=O>CC(=O)OCC>[NH2:6][C:9]1[CH:10]=[C:11]([C:18]([F:21])([F:19])[F:20])[C:12]([CH2:15][C:16]#[N:17])=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 904161702-(5-Nitro-3-(trifluoromethyl)pyridin-2-yl)acetonitrile

Product 1

HCID 904165325-Amino-3-(trifluoromethyl)pyridine-2-acetonitrileYield 61.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A suspension of tin(II) chloride dihydrate (58.6 mg, 0.260 mmol) in EA (60 mL) was added to a solution of 2-(5-nitro-3-(trifluoromethyl)pyridin-2-yl)acetonitrile (30 mg, 0.130 mmol) in EA (60 mL). The mixture was at 50° C. for 3 h. Then the solution was concentrated and distributed between EA and saturated NaHCO3 solution. The combined organic extract was washed with brine, dried over MgSO4, filtered and concentrated. The resulting 2-(5-amino-3-(trifluoromethyl)pyridin-2-yl)acetonitrile (16 mg, 0.080 mmol, 61.3% yield) was used in the next step without further purification. TLC (PE/EA=1:1, Rf=0.5): 1H NMR (400 MHz, CDCl3) δ: 8.19-8.27 (m, 1H), 7.22 (d, J=2.5 Hz, 1H), 3.97 (s, 2H); ES-LCMS m/z 202.0 (M+H).

Workup

  1. concentrationThen the solution was concentrated
  2. extractionThe combined organic extract
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-58380242e36d4b84939dfa60fc60744f
Source dataset
uspto-grants-2015_05
Patent number
US09035063B2

Reaction notes

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