Methylamine → 6-chloro-N-methyl-3-nitropyridin-2-amine

HRID 1362907Notes

Reaction equation

HRID 1362907 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[CH3:12][NH2:13].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O>[Cl:11][C:4]1[N:3]=[C:2]([NH:13][CH3:12])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 10340Sodium CarbonateHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 107500946-chloro-N-methyl-3-nitropyridin-2-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 10 g (52 mmol) of 2,6-dichloro-3-nitropyridine in 300 mL of N,N-dimethylformamide was added 26 mL (52 mmol) of methylamine (2M in tetrahydrofuran) and 9.3 g (88 mmol) of sodium carbonate and the resulting mixture was stirred for 24 h. The solution was diluted with 500 mL water and extracted with three 700 mL portions of ethyl acetate. The organic phase was dried over magnesium sulfate, filtered, and evaporated in vacuo to yield a viscous oil. The crude material was purified by flash chromatography on a Biotage Horizon® system (silica gel, 0 to 10% ethyl acetate/hexanes gradient) to give 6-chloro-N-methyl-3-nitropyridin-2-amine as a yellow solid. LC/MS 188.1 (M+1).

Workup

  1. extractionextracted with three 700 mL portions of ethyl acetate
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customto yield a viscous oil
  6. customThe crude material was purified by flash chromatography on a Biotage Horizon® system (silica gel, 0 to 10% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-a8303d5052f2474484503cb2f1c27f96
Source dataset
uspto-grants-2011_02
Patent number
US07884104B2

Reaction notes

Loading…