Formaldehyde → HCID 59405005, compound

HRID 1892197Notes

Reaction equation

HRID 1892197 reaction equation
[CH3:1][C:2]1([CH3:18])[C:7]([C:8]2[CH:9]=[N:10][C:11]([CH3:17])=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=2)=[CH:6][CH2:5][NH:4][CH2:3]1.C=O.[C:21](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:21][N:4]1[CH2:5][CH:6]=[C:7]([C:8]2[CH:9]=[N:10][C:11]([CH3:17])=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=2)[C:2]([CH3:18])([CH3:1])[CH2:3]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 673367223',3',6-Trimethyl-5-nitro-1',2',3',6'-tetrahydro-3,4'-bipyridine

Product 1

HCID 59405005HCID 59405005, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3′,3′,6-trimethyl-5-nitro-1′,2′,3′,6′-tetrahydro-3,4′-bipyridine [HCl] (1.12 g, 3.50 mmol) in DCM (55 mL) were added formaldehyde (37% in water, 4.0 mL) and sodium triacetoxyborohydride (4.45 g, 21.0 mmol). The reaction mixture was allowed to stir for 2 h at rt. The mixture was quenched by the addition of sat. aq. sodium bicarbonate (40 mL). After stirring for 10 min, the aqueous solution was extracted with DCM. The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 1′,3′,3′,6-tetramethyl-5-nitro-1′,2′,3′,6′-tetrahydro-3,4′-bipyridine (0.914 g, 100%). LCMS (FA): Rt=0.85 min, m/z=262.4 (M+H).

Workup

  1. customThe mixture was quenched by the addition of sat. aq. sodium bicarbonate (40 mL)
  2. stirringAfter stirring for 10 min
  3. extractionthe aqueous solution was extracted with DCM
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-333454b350f24f0ca73b7707b0f4424b
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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