Nitric Acid → N,N-Diethyl-6-methyl-5-nitro-2-pyridinamine
Reaction equation
[CH2:1]([N:3]([CH2:11][CH3:12])[C:4]1[N:9]=[C:8]([CH3:10])[CH:7]=[CH:6][CH:5]=1)[CH3:2].[N+:13]([O-])([OH:15])=[O:14].[OH-].[Na+]>S(=O)(=O)(O)O>[CH2:11]([N:3]([CH2:1][CH3:2])[C:4]1[N:9]=[C:8]([CH3:10])[C:7]([N+:13]([O-:15])=[O:14])=[CH:6][CH:5]=1)[CH3:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
To a 1900 ml of concentrated sulfuric acid 630 g of 6-diethylamino-2-picoline were dropwise added while cooling with ice water. A 70% nitric acid solution of 347 g were dropwise added at not more than 5° C. over about 2 hours to the resulting mixture and stirred at 5° C. for additional one hour. The reation mixture was added to 4 kg of ice, neutralized with a sodium hydroxide solution, and extracted two times with ethyl acetate. The extract solution was washed two times with water, dried over anhydrous magnesium sulfate, concentrated and dried. Thus, 775 g of 6-diethylamino-3-nitro-2-picoline were obtained.
Workup
- extractionextracted two times with ethyl acetate
- washThe extract solution was washed two times with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- customdried
Sources & evidence
- ORD record
- ord-cce2ebf2d6ed4271bbe8fba480dd9795
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05753017
Reaction notes
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