Hydrochloric Acid → 3',3',6-Trimethyl-5-nitro-1',2',3',6'-tetrahydro-3,4'-bipyridine

HRID 1892196Notes

Reaction equation

HRID 1892196 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:15]=[N:16][C:17]([CH3:23])=[C:18]([N+:20]([O-:22])=[O:21])[CH:19]=2)[C:10]([CH3:25])([CH3:24])[CH2:9]1)=O)(C)(C)C.Cl>CO>[CH3:24][C:10]1([CH3:25])[C:11]([C:14]2[CH:15]=[N:16][C:17]([CH3:23])=[C:18]([N+:20]([O-:22])=[O:21])[CH:19]=2)=[CH:12][CH2:13][NH:8][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59404975HCID 59404975, compound

Product 1

HCID 673367223',3',6-Trimethyl-5-nitro-1',2',3',6'-tetrahydro-3,4'-bipyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl-3′,3′,6-trimethyl-5-nitro-3′,6′-dihydro-3,4′-bipyridine-1′(2′H)-carboxylate (1.30 g, 3.70 mmol) in MeOH (30 mL) was added hydrochloric acid (4.0 M in 1,4-dioxane, 40 mL). The reaction mixture was allowed to stir for 2 h at rt. The reaction mixture was concentrated to give 3′,3′,6-trimethyl-5-nitro-1′,2′,3′,6′-tetrahydro-3,4′-bipyridine as the hydrochloride salt (1.12 g, 100%) as a white solid. LCMS (FA): Rt=0.89 min, m/z=248.3 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-0ede7df37b284ec8bc60cd1d585b93df
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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