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

HRID 1398858Notes

Reaction equation

HRID 1398858 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-f3fb8a39dac94f489ff115c56b216c99
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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