Dimethylamine → N,N,6-trimethyl-5-nitropyridin-2-amine

HRID 510478Notes

Reaction equation

HRID 510478 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.[CH3:12][NH:13][CH3:14].O>CO.CCOC(C)=O>[CH3:12][N:13]([CH3:14])[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[N:7]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 2531236-Chloro-2-methyl-3-nitropyridine

Product 1

HCID 59613085N,N,6-trimethyl-5-nitropyridin-2-amineYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6-chloro-2-methyl-3-nitropyridine (0.5 g, 2.9 mmol) in MeOH (5 mL) was added dimethylamine in water (1.2 mL, 11.6 mmol) and the reaction mixture was heated at 60° C. for 4 h. The reaction mixture was then diluted with EtOAc, extracted with water and washed with brine. The organic layer was dried over sodium sulphate and concentrated to yield the title compound (0.5 g, 95%). LCMS (ES+) 182 (M+H)+, RT 2.74 minutes (method 1).

Workup

  1. extractionextracted with water
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-641d5a0c95c447e99b22c2fceee344cb
Source dataset
uspto-grants-2015_08
Patent number
US09096614B2

Reaction notes

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