Acetic Acid → 5-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-nitropyridine

HRID 1022012Notes

Reaction equation

HRID 1022012 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH:15]=2)=[CH:6][N:5]=1)([O-:3])=[O:2].C=O.[C:18](O)(=O)C>CO>[CH3:18][N:13]1[CH2:12][CH:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[N:5][CH:6]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 712FormaldehydeHCID 866844372-Nitro-5-(1,2,3,6-tetrahydropyridin-4-yl)pyridine

Product 1

HCID 580442465-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-nitropyridineYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 232a (1.2 g, 5.8 mmol) in CH3OH (25 mL) was added HCHO (1 mL, 35 mmol) and acetic acid (1 mL), followed by the addition of NaBHCN3 (1.0 g, 12 mmol). The mixture was stirred at room temperature for 2 h. It was then evaporated under reduced pressure and the residue was purified by reverse-phase Combiflush eluting with 0.3% NH4HCO3 in water/acetonitrile to afford 232b as a yellow solid (1.0 g, 78%). MS-ESI: [M+H]+ 220.

Workup

  1. additionfollowed by the addition of NaBHCN3 (1.0 g, 12 mmol)
  2. customIt was then evaporated under reduced pressure
  3. customthe residue was purified by reverse-phase Combiflush
  4. washeluting with 0.3% NH4HCO3 in water/acetonitrile

Sources & evidence

ORD record
ord-d38a7f35d18a4c04a0c9a6c023d75c40
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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