Ammonia → N-tert-Butyl-3-methylpyridine-2-carboxamide
Reaction equation
[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].S(=O)(=O)(O)[OH:11].[C:15]1([CH3:21])[CH:20]=CC=C[CH:16]=1.N>CC(O)(C)C.O>[CH3:16][C:15]([NH:2][C:1]([C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:11])([CH3:21])[CH3:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
2-cyano-3-methyl pyridine (400 g) is suspended in t-BuOH (800 mL) and the mixture heated to 70° C. Concentrated sulphuric acid (400 mL) is added dropwise over 45 minutes. The reaction is complete after a further 30 minutes at 75° C. The mixture is then diluted with water (400 mL), charged with toluene (600 mL) and brought to pH 10 with concentrated aqueous ammonia. The temperature is kept at 50°-55° C. during the work up. The toluene phase is separated, the aqueous layer reextracted and the combined toluene phases are washed with water. Removal of the toluene yields an oil, N-(1,1-dimethylethyl)-3-methyl-2-pyridine carboxamide, from which solid product may crystallize. Product yield of 97% is determined by internal standard assay on gas chromatograph.
Workup
- customis kept at 50°-55° C. during the work
- customThe toluene phase is separated
- washthe combined toluene phases are washed with water
- customRemoval of the toluene
Sources & evidence
- ORD record
- ord-becfb2b95d864db7b15047cc42b826f9
- Source dataset
- uspto-grants-1987_04
- Patent number
- US04659716
Reaction notes
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