Water → 2,5-Dichloro-6-methoxy-4-methylnicotinonitrile
Reaction equation
[Cl:1][C:2]1[N:9]=[C:8](Cl)[C:7]([Cl:11])=[C:6]([CH3:12])[C:3]=1[C:4]#[N:5].[CH3:13][O-:14].[Na+].O>CO>[Cl:1][C:2]1[N:9]=[C:8]([O:14][CH3:13])[C:7]([Cl:11])=[C:6]([CH3:12])[C:3]=1[C:4]#[N:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a slurry of 2,5,6-trichloro-4-methyl-nicotinonitrile (11.0 g, 49.67 mmol, Tetrahedron, 1977, 33, 113-117) in MeOH (125 ml) is added sodium methoxide solution (25% wt. in MeOH)(11.92 ml, 52.15 mmol). The reaction mixture is stirred at 0° C. for 30 minutes, then room temperature for 1 hour. The reaction is quenched by the addition of water (300 ml) and a thick, white precipitate is formed. An additional 200 ml of water is added and the mixture is stirred at 0° C. for 10 minutes. The precipitate is collected by filtration and dried (vacuum oven for 16 hours at 60° C.) to give the title compound as an off-white solid (10.05 g, 93%). Mass (m/z): 217.0 (M++1).
Workup
- waitroom temperature for 1 hour
- customThe reaction is quenched by the addition of water (300 ml)
- customa thick, white precipitate is formed
- stirringthe mixture is stirred at 0° C. for 10 minutes
- filtrationThe precipitate is collected by filtration
- customdried (vacuum oven for 16 hours at 60° C.)
Sources & evidence
- ORD record
- ord-d6499da99bf3479daa68671392cd9511
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071776B2
Reaction notes
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