Stannous chloride dihydrate → HCID 90416701, compound

HRID 576170Notes

Reaction equation

HRID 576170 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][C:7]([N+:14]([O-])=O)=[CH:6][N:5]=1)[CH3:2].O.O.[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>CC(=O)OCC>[CH2:1]([O:3][C:4]1[N:5]=[CH:6][C:7]([NH2:14])=[CH:8][C:9]=1[C:10]([F:13])([F:11])[F:12])[CH3:2]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 90417610HCID 90417610, compound

Product 1

HCID 90416701HCID 90416701, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
50 °C

Procedure

To a mixture of 2-ethoxy-5-nitro-3-(trifluoromethyl)pyridine (120 mg, 0.508 mmol) in EA (10 mL) was added tin(II) chloride dihydrate (459 mg, 2.033 mmol). The mixture was stirred at 50° C. for 16 h. Then the solution was distributed between EA and saturated NaHCO3 solution. The combined organic extract was washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by preparative TLC (PE/EA=4:1, Rf=0.6) to yield a light yellow oil of 6-ethoxy-5-(trifluoromethyl)pyridin-3-amine (80 mg, 0.310 mmol, 61.1% yield): 1H NMR (400 MHz, CD3OD) δ 6.27 (d, J=2.5 Hz, 1H), 5.86 (d, J=3.0 Hz, 1H), 2.81 (m, 2H), 0.17 (t, J=7.0 Hz, 3H); ES-LCMS m/z 207.1 (M+H).

Workup

  1. extractionThe combined organic extract
  2. washwas washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by preparative TLC (PE/EA=4:1, Rf=0.6)

Sources & evidence

ORD record
ord-42ae75036e3d466f941c252f83043c54
Source dataset
uspto-grants-2015_05
Patent number
US09035063B2

Reaction notes

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