Phosphorus oxychloride → 6-Chloro-3-methylpyridine-2-carbonitrile

HRID 1799552Notes

Reaction equation

HRID 1799552 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[N+:4]([O-])[C:3]=1[C:9]#[N:10].O=P(Cl)(Cl)[Cl:13]>>[Cl:13][C:5]1[N:4]=[C:3]([C:9]#[N:10])[C:2]([CH3:1])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 450798222-Cyano-3-methylpyridine 1-oxide

Product 1

HCID 468562786-Chloro-3-methylpyridine-2-carbonitrile

Procedure

3-Methylpyridine-2-carbonitrile 1-oxide (8.42 g, 62.8 mmol) was stirred in refluxing POCl3 (60 mL, 646 mmol) for 6 hours. The mixture was cooled to room temperature and slowly poured into ice-water. The resulting beige precipitate was collected by filtration to give the title compound.

Workup

  1. filtrationThe resulting beige precipitate was collected by filtration

Sources & evidence

ORD record
ord-bae3a1eea51b45be8ab5aab6641cd751
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

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