Chlorosulfonic acid → HCID 178524660, compound

HRID 1992072Notes

Reaction equation

HRID 1992072 reaction equation
[OH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:11][S:12](O)(=[O:14])=[O:13]>>[Cl:11][S:12]([C:8]1[CH:9]=[N:10][C:2]([OH:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])(=[O:14])=[O:13]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 178418543HCID 178418543, compound

Product 1

HCID 178524660HCID 178524660, compoundYield 44%

Conditions

Temperature
160 °C

Procedure

2-Hydroxynicotinic acid (10.0 g, 71.8 mmol) was dissolved in 25 ml of chlorosulfonic acid and heated to 160° C. overnight. After cooling the reaction was slowly poured into ice and stirred in an ice bath until a white precipitate formed. The solid was filtered off and dried under vacuum to afford 7.55 g of 5-(chlorosulfonyl)-2-hydroxynicotinic acid (44% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 7.9 (dd, J=2.5, 0.7 Hz, 1H) 8.4 (dd, J=2.6, 0.7 Hz, 1H).

Workup

  1. temperatureAfter cooling the reaction
  2. additionwas slowly poured into ice
  3. customformed
  4. filtrationThe solid was filtered off
  5. customdried under vacuum

Sources & evidence

ORD record
ord-7124389b873741a48a2103f353314827
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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