Phosphorus oxychloride → 6-Chloro-2-methylnicotinonitrile

HRID 241688Notes

Reaction equation

HRID 241688 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]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 113785166-Hydroxy-2-methylnicotinonitrile

Product 1

HCID 123877376-Chloro-2-methylnicotinonitrile

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

  1. temperaturewas refluxed for 3 h
  2. customThe reaction mixture was dried down in vacuum and ice
  3. additionwas added
  4. extractionThe aqueous layer was extracted with EtOAc
  5. customThe organic layer was separated
  6. customdried
  7. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-2b5428a5670845489790d812dc7b0690
Source dataset
uspto-grants-2014_02
Patent number
US08653075B2

Reaction notes

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