Fuming sulfuric acid → HCID 178524662, compound

HRID 2307255Notes

Reaction equation

HRID 2307255 reaction equation
[OH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH:11][S:12](O)(=[O:14])=[O:13].O=S(=O)=O>>[OH:1][C:2]1[N:10]=[CH:9][C:8]([S:12]([OH:14])(=[O:13])=[O:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

3

Reactant 2

HCID 24681Fuming sulfuric acidHCID 178418543HCID 178418543, compound

Product 1

HCID 178524662HCID 178524662, compound

Conditions

Temperature
140 °C

Procedure

2-Hydroxynicotinic acid (27 Kg, 194.2 mol) was added portionwise to 30% oleum (58.1 Kg) at 50° C. over 1 hour. This caused an exotherm to 82° C. The reaction mixture was heated further to 140° C. After maintaining this temperature for 12 hours the reactor contents were cooled to 15° C. and filtered. The filter cake was then re-slurried with acetone (33 Kg) at room temperature, filtered and dried to afford the title compound, 35.3 Kg, as a white solid.

Workup

  1. customto 82° C
  2. temperatureAfter maintaining this temperature for 12 hours the reactor contents
  3. temperaturewere cooled to 15° C.
  4. filtrationfiltered
  5. filtrationre-slurried with acetone (33 Kg) at room temperature, filtered
  6. customdried

Sources & evidence

ORD record
ord-2c7568d6064a41dc9f1b592da6fb7556
Source dataset
uspto-grants-2004_12
Patent number
US06831074B2

Reaction notes

Loading…