Hydrochloric Acid → [2,3'-Bipyridin]-5'-ylmethanamine

HRID 2111683Notes

Reaction equation

HRID 2111683 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:8]=1)#[N:2].Cl>C(O)C.CO.[Pd]>[NH2:2][CH2:1][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:8]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 23342325[2,3'-Bipyridine]-5'-carbonitrile

Product 1

HCID 67285184[2,3'-Bipyridin]-5'-ylmethanamineYield 79.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

2-(3-Cyanopyridin-5-yl)pyridine (Method 101; 0.98 g, 5.4 mmol) was dissolved in a mixture of ethanol (45 ml) and methanol (30 ml). Concentrated hydrochloric acid (1.2 ml) and 10% palladium on carbon catalyst (575 mg) were added and the mixture stirred under an atmosphere of hydrogen for 4 hours. The mixture was filtered through diatomaceous earth, the filter pad washed with ethanol and the volatiles removed from the filtrate by evaporation. The crude solid was suspended in a small volume of methanol and filtered to give the title compound (794 mg, 66%) as an orange solid. NMR (DMSO): 4.31 (m, 2H) 7.58 (t, 1H), 8.09 (t, 1H), 8.24 (d, 1H), 8.78 (d, 1H), 8.89 (bs, 2H), 9.03 (s, 1H), 9.26 (s, 1H), 9.43 (s, 1H); m/z 186 (MH)+.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. washthe filter pad washed with ethanol
  3. customthe volatiles removed from the filtrate by evaporation
  4. filtrationfiltered

Sources & evidence

ORD record
ord-a872992b4e9a4b55bad9a19ef417da21
Source dataset
uspto-grants-2009_04
Patent number
US07521453B2

Reaction notes

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