Phosphorus oxychloride → 2-Chloro-4,6-dimethyl-3-pyridinecarbonitrile

HRID 705171Notes

Reaction equation

HRID 705171 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=O)[C:3]=1[C:10]#[N:11].P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:4]1[N:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[C:3]=1[C:10]#[N:11]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 698563-Cyano-4,6-dimethyl-2-hydroxypyridine

Product 1

HCID 2232612-Chloro-4,6-dimethyl-3-pyridinecarbonitrileYield 90%

Procedure

4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (5 g, 34 mmol) was added to phosphorus oxychloride (20 ml). The reaction was stirred at reflux for 2 h, after which it was seen complete. Volatiles were removed and the residue triturated with petrol. The resultant solid was filtered off and washed with hexane, and dried to give a pure white solid (5.1 g, 90%). δH (250 MHz, CDCl3) 2.55 (3 H, s, CH3), 2.57 (3 H, s, CH3), 7.09 (1 H, s, ArH); δC (250 MHz, CDCl3) 162.64 (C), 154.39 (C), 152.26 (C), 123.22 (CH), 114.28 (C), 108.31 (C), 24.5 (CH3), 20.54 (CH3); m/z 189 (M+Na)

Workup

  1. temperatureat reflux for 2 h
  2. customVolatiles were removed
  3. customthe residue triturated with petrol
  4. filtrationThe resultant solid was filtered off
  5. washwashed with hexane
  6. customdried

Sources & evidence

ORD record
ord-d54d83dd09ce43c1892398640da6184b
Source dataset
uspto-grants-2015_11
Patent number
US09173938B2

Reaction notes

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