tert-Butyl 6-nitro-3',6'-dihydro-[3,4'-bipyridine]-1'(2'H)-carboxylate → 2-Nitro-5-(1,2,3,6-tetrahydropyridin-4-yl)pyridine

HRID 1022011Notes

Reaction equation

HRID 1022011 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([C:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]>Cl.O1CCOCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH:11]=2)=[CH:8][N:9]=1)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 49840377tert-Butyl 6-nitro-3',6'-dihydro-[3,4'-bipyridine]-1'(2'H)-carboxylate

Product 1

HCID 866844372-Nitro-5-(1,2,3,6-tetrahydropyridin-4-yl)pyridineYield 74%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A mixture of tert-butyl 4-(6-nitropyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate 200a (2.0 g, 6.6 mmol) in HCl/dioxane (20 mL, 4M) was stirred at room temperature for 2 hours. It was then evaporated under reduced pressure. The residue was washed with ethyl acetate (3×7 mL) to afford 232a as a yellow solid (1.0 g, 74%). MS-ESI: [M+H]+ 206.

Workup

  1. customIt was then evaporated under reduced pressure
  2. washThe residue was washed with ethyl acetate (3×7 mL)

Sources & evidence

ORD record
ord-621f81d8187341b3ad5087c811bed69a
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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