Phosphorus oxychloride → 2-Chloro-5-(chlorosulfonyl)pyridine-3-carboxylic acid

HRID 1992073Notes

Reaction equation

HRID 1992073 reaction equation
[Cl:1][S:2]([C:5]1[CH:6]=[N:7][C:8](O)=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])(=[O:4])=[O:3].O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:8]1[N:7]=[CH:6][C:5]([S:2]([Cl:1])(=[O:4])=[O:3])=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178524660HCID 178524660, compound

Product 1

HCID 574159692-Chloro-5-(chlorosulfonyl)pyridine-3-carboxylic acid

Conditions

Temperature
130 °C

Procedure

5-(Chlorosulfonyl)-2-hydroxynicotinic acid (500 mg, 2.10 mmol) vas suspended in 5 ml of POCl3 in a sealed tube and heated to 130° C. until all solid had dissolved. The reaction was cooled to 0° C. and poured onto ice and stirred until a solid formed. The filtered white solid was dried to afford 2-chloro-5-(chlorosulfonyl)nicotinic acid. 1H NMR (400 MHz, Acetone-d6) δ ppm 8.9 (d, J=2.6 Hz, 10H), 9.3 (d, J=2.6 Hz, 10H).

Workup

  1. dissolutionhad dissolved
  2. temperatureThe reaction was cooled to 0° C.
  3. additionpoured onto ice
  4. customformed
  5. customThe filtered white solid was dried

Sources & evidence

ORD record
ord-63dcb4723f3544288a60808636bcfd50
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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