Sodium borohydride → Amino(pyridin-3-yl)acetonitrile

HRID 744598Notes

Reaction equation

HRID 744598 reaction equation
[BH4-].[Na+].[I-].C(O[C:9]1[C:10]([C:14]2[CH:15]=[N+:16](C)[CH:17]=[CH:18][CH:19]=2)=[N:11]S[N:13]=1)CCC>C(O)C>[NH2:11][CH:10]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[C:9]#[N:13]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19075249131988-14-2

Product 1

HCID 15180125Amino(pyridin-3-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (240 mg, 6.4 mmol) was added to a solution of 3-(4-butoxy-1,2,5-thiadiazol-3-yl)-1-methylpyridinium iodide (0.60 g, 1.6 mmol) in ethanol (99.9%, 20 ml) and the reaction mixture was stirred at 0° C. for 1 h. After evaporation the residue was dissolved in water and extracted with ethyl acetate. The dried organic phases were evaporated and the residue purified by column chromatography (SiO2, eluent: ethyl acetate/methanol (4:1)). The title compound was crystallized as the oxalate salt from acetone to yield 280 mg (M.p 158° C.; M+ : 253; Compound 4).

Workup

  1. customAfter evaporation the residue
  2. dissolutionwas dissolved in water
  3. extractionextracted with ethyl acetate
  4. customThe dried organic phases were evaporated
  5. customthe residue purified by column chromatography (SiO2, eluent: ethyl acetate/methanol (4:1))
  6. customThe title compound was crystallized as the oxalate salt from acetone

Sources & evidence

ORD record
ord-b38b2fc5492b4c39aa27be4f2112a67d
Source dataset
uspto-grants-1996_09
Patent number
US05559138

Reaction notes

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