Dimethylamine, hydrochloride → HCID 59405027, compound

HRID 1892211Notes

Reaction equation

HRID 1892211 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[C:6]([CH3:9])=[N:7][CH:8]=1)#[CH:2].Cl.[CH3:14][NH:15][CH3:16].C([BH3-])#N.[Na+]>CCO>[CH3:14][N:15]([CH3:16])[CH2:2][CH2:1][C:3]1[CH:8]=[N:7][C:6]([CH3:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 58476611HCID 58476611, compound

Product 1

HCID 59405027HCID 59405027, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-ethynyl-2-methyl-3-nitropyridine (930 mg, 5.74 mmol) in EtOH (7 mL) were added dimethylamine hydrochloride (2.34 g, 28.7 mmol) and sodium cyanoborohydride (0.721 g, 11.5 mmol). The reaction mixture was allowed to stir at reflux for 24 h, concentrated, and treated with 4N NaOH (10 mL). The solution was extracted with DCM (2×200 mL). The organic solutions were combined, washed with brine (200 mL), dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give N,N-dimethyl-2-(6-methyl-5-nitropyridin-3-yl)ethanamine (489 mg, 41%). LCMS (AA): Rt=1.35 min, m/z=210 (M+H).

Workup

  1. temperatureat reflux for 24 h
  2. concentrationconcentrated
  3. additiontreated with 4N NaOH (10 mL)
  4. extractionThe solution was extracted with DCM (2×200 mL)
  5. washwashed with brine (200 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-fc76feb3dbd04c6fb9c7f87e4c2d59ab
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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