Formaldehyde → HCID 59405005, compound

HRID 2387998Notes

Reaction equation

HRID 2387998 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-d8239880ec1c432fb7ca9c83c317970d
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

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