Hydrochloric Acid → N-benzyl-N-methyl-3-nitropyridin-2-amine

HRID 587501Notes

Reaction equation

HRID 587501 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:17][NH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[Cl-].[Ca+2].Cl>C1COCC1>[CH2:19]([N:18]([CH3:17])[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7669N-MethylbenzylamineHCID 10340Sodium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 5284359Calcium Chloride

Product 1

HCID 9211491N-benzyl-N-methyl-3-nitropyridin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 2-chloro-3-nitropyridine (15 g), Na2CO3 (10.03 g) and N-methylbenzylamine (24.42 mL) in THF (150 mL) was stirred at 80° C. under a dry atmosphere (CaCl2 tube) overnight. The mixture was neutralized with 1N HCl at 0° C. and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 0%-30% EtOAc in hexane) to give N-benzyl-N-methyl-3-nitropyridin-2-amine (19 g) as yellow oil.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel, eluted with 0%-30% EtOAc in hexane)

Sources & evidence

ORD record
ord-2149e8f1e4284eed8195c6cb6bedfc19
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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