Stannous chloride dihydrate → 2-(5-Amino-3-(trifluoromethyl)pyridin-2-yl)propanenitrile

HRID 1428612Notes

Reaction equation

HRID 1428612 reaction equation
O.O.[Sn](Cl)Cl.[N+:6]([C:9]1[CH:10]=[C:11]([C:19]([F:22])([F:21])[F:20])[C:12]([CH:15]([CH3:18])[C:16]#[N:17])=[N:13][CH:14]=1)([O-])=O>CC(=O)OCC>[NH2:6][C:9]1[CH:10]=[C:11]([C:19]([F:22])([F:20])[F:21])[C:12]([CH:15]([CH3:18])[C:16]#[N:17])=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 904165882-(5-Nitro-3-(trifluoromethyl)pyridin-2-yl)propanenitrile

Product 1

HCID 904158462-(5-Amino-3-(trifluoromethyl)pyridin-2-yl)propanenitrileYield 85.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Tin(II) chloride dihydrate (135 mg, 0.600 mmol) was added to a solution of 2-(5-nitro-3-(trifluoromethyl)pyridin-2-yl)propanenitrile (73.6 mg, 0.300 mmol) in EA (15 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)propanenitrile (55 mg, 0.256 mmol, 85.0% yield) was used to next step without further purification. TLC (PE/EA=5:1, Rf=0.5): 1H NMR (400 MHz, CDCl3) δ: 8.25 (s, 1H), 7.17 (d, J=2.2 Hz, 1H), 4.15-4.28 (m, 1H), 1.66 (d, J=7.1 Hz, 3H); ES-LCMS m/z 216.0 (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-d04fb357decb4e71938d20c6d68edbb4
Source dataset
uspto-grants-2015_01
Patent number
US08937071B2

Reaction notes

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