Phosphorus oxychloride → 6-Chloro-2-methylnicotinonitrile
Reaction equation
[CH3:1][C:2]1[NH:3][C:4](=O)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].O=P(Cl)(Cl)[Cl:13]>>[Cl:13][C:4]1[CH:5]=[CH:6][C:7]([C:8]#[N:9])=[C:2]([CH3:1])[N:3]=1Participants
3
Procedure
A mixture of 2-Methyl-6-oxo-1,6-dihydro-pyridine-3-carbonitrile (44 g) and POCl3 (250 ml) was refluxed for 3 h. The reaction mixture was dried down in vacuum and ice followed by conc. aqueous ammonia (300 ml) was added. The aqueous layer was extracted with EtOAc. The organic layer was separated, dried and concentrated in vacuum affording the title compound (23.5 g, BP (18 mbar) 119-120° C.).
Workup
- temperaturewas refluxed for 3 h
- customThe reaction mixture was dried down in vacuum and ice
- additionwas added
- extractionThe aqueous layer was extracted with EtOAc
- customThe organic layer was separated
- customdried
- concentrationconcentrated in vacuum
Sources & evidence
- ORD record
- ord-2b5428a5670845489790d812dc7b0690
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653075B2
Reaction notes
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