Ethanol → HCID 67608342, compound

HRID 925289Notes

Reaction equation

HRID 925289 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]#[N:10])[N:6]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:4]=1.C([O-])=O.[NH4+].C(O)C>O.[OH-].[Pd+2].[OH-].[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH2:10])[N:6]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:4]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 2723923Ammonium formateHCID 135867984-Methoxy[2,2′-bipyridine]-6-carbonitrile

Product 1

HCID 67608342HCID 67608342, compound

Reagents, catalysts & solvents 2

HCID 86707187HCID 86707187, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
27 °C

Procedure

A mixture of 4-Methoxy-[2,2′]bipyridinyl-6-carbonitrile (1.0 g, 4.73 mmol), Palladium hydroxide-Pd 20%-50% in water (0.66 g, excess), ammonium formate (1.5 g, excess) and ethanol (60 mL) was stirred at 27° C. for 2 hours. The reaction was then filtered thorough celite, washed with methanol (150 mL) and dichloromethane (150 mL) and the organic phase evaporated to dryness affording C-(4-Methoxy-[2,2′]bipyridinyl-6-yl)-methylamine as an orange oil (0.80 g, 45%, in a ratio 72 to 28 product vs. byproduct).

Workup

  1. filtrationThe reaction was then filtered thorough celite
  2. washwashed with methanol (150 mL) and dichloromethane (150 mL)
  3. customthe organic phase evaporated to dryness

Sources & evidence

ORD record
ord-10b15ff6da5b48f09413dff1e52b33f7
Source dataset
uspto-grants-2016_03
Patent number
US09284296B2

Reaction notes

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