Dimethylamine → N,N,4-Trimethyl-5-nitropyridin-2-amine

HRID 1628505Notes

Reaction equation

HRID 1628505 reaction equation
[CH3:1][NH:2][CH3:3].Cl[C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][N:6]=1>O1CCCC1>[CH3:1][N:2]([CH3:3])[C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 3453642-Chloro-4-methyl-5-nitropyridine

Product 1

HCID 21857174N,N,4-Trimethyl-5-nitropyridin-2-amineYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dimethylamine (50% solution in water, 20 mL) was added to a stirred solution of 2-chloro-4-methyl-5-nitropyridine (15.0 g, 86.9 mmol) in tetrahydrofuran (150 mL), and the mixture was stirred at 0° C. for 2 hr. The mixture was concentrated in vacuo, diluted with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the title compound as a yellow solid (15.7 g, 86.6 mmol, 99%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with saturated aqueous sodium hydrogen carbonate
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-10ff3fb2e3f64583826c6c984fb20f43
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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