Dimethylformamide → 2-(2-Dimethylaminoethen-2-yl)-3-nitro-6-methoxypyridine
Reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH3:9])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][CH:4]=1.CO[CH:15](OC)[N:16](C)[CH3:17].[CH3:21]N(C)C=O>>[CH3:15][N:16]([CH3:17])[C:9]([C:7]1[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:8]=1)=[CH2:21]Participants
4
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 2.0 gm (11.9 mMol) 6-methoxy-3-nitro-2-picoline and 16 mL (119 mMol) dimethylformamide dimethylacetal in 20 mL dimethylformamide was heated at 100° C. for 7 hours. The reaction mixture was concentrated under reduced pressure. The residue was treated with toluene and concentrated under reduced pressure. The residual solid was dried at 50° C. under reduced pressure for 1 hour to provide 2.70 gm (100%) of the desired compound as a red solid.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionThe residue was treated with toluene
- concentrationconcentrated under reduced pressure
- customThe residual solid was dried at 50° C. under reduced pressure for 1 hour
Sources & evidence
- ORD record
- ord-27ee9c0cf4c14fe4810b0e12b75199f2
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05874427
Reaction notes
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