Dichloromethane → 3-(2-Pyridyl)-5-(3-amino-5-cyanophenyl)-1,2,4-oxadiazole

HRID 431966Notes

Reaction equation

HRID 431966 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[C:14]([C:21]#[N:22])[CH:13]=2)[O:9][N:8]=1.O.O.[Sn](Cl)Cl.ClCCl>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:13]=[C:14]([C:21]#[N:22])[CH:15]=[C:16]([NH2:18])[CH:17]=2)[O:9][N:8]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 61436Stannous chloride dihydrateHCID 219425113-(2-Pyridyl)-5-(3-cyano-5-nitrophenyl)-1,2,4-oxadiazole

Product 1

HCID 219426193-(2-Pyridyl)-5-(3-amino-5-cyanophenyl)-1,2,4-oxadiazoleYield 10.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(2-Pyridyl)-5-(3-cyano-5-nitrophenyl)-1,2,4-oxadiazole (30 mg, 0.10 mmol) and tin(II) chloride dihydrate (115 mg, 0.51 mmol) in ethanol (1 mL) were sealed in a glass vial and then heated at 78 oC for 2 hours. The reaction was cooled and dichloromethane was added to the reaction mixture. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Silica gel chromatography of the residue using hexanes:ethyl acetate:dichloromethane 1:3:4 followed by recrystallization using methanol afforded 2.8 mg (10%) of 3-(2-Pyridyl)-5-(3-amino-5-cyanophenyl)-1,2,4-oxadiazole: 1H NMR (CDCl3), δ (ppm): 8.85 (d, 1H), 8.22 (d, 1H), 7.91 (m, 2H), 7.78 (s, 1H), 7.48 (m, 1H), 7.11 (s, 1H), 4.17 (bs, 2H).

Workup

  1. temperatureheated at 78 oC for 2 hours
  2. temperatureThe reaction was cooled
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customfollowed by recrystallization

Sources & evidence

ORD record
ord-55a7ca866e054b34b363d8ea3c16f778
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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