Phosphorus oxychloride → 2-Chloro-6-methylnicotinic acid

HRID 1979607Notes

Reaction equation

HRID 1979607 reaction equation
O[C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178425908HCID 178425908, compound

Product 1

HCID 1217242-Chloro-6-methylnicotinic acidYield 72%

Procedure

2-Hydroxy-6-methyl-nicotinic acid (3.6 g, 0.02 m) was heated at 125° for 2 hours with phosphorus oxychloride (10 ml). The reaction mixture was poured onto ice, the solid was collected and crystallised from aqueous ethanol to give colourless fine needles of 2-chloro-6-methylnicotinic acid (72%).

Workup

  1. additionThe reaction mixture was poured onto ice
  2. customthe solid was collected
  3. customcrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-5f407a3f9ebe4e37846e9c607f5d805e
Source dataset
uspto-grants-1984_11
Patent number
US04481268

Reaction notes

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