Fuming sulfuric acid → HCID 178524662, compound

HRID 892223Notes

Reaction equation

HRID 892223 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, compoundYield 83%

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 hr. This caused an exotherm to 82° C. The reaction mixture was heated further to 140° C. After maintaining this temperature for 12 hrs the reactor contents were cooled to 15C and filtered. The filter cake was then re-slurried with acetone (33 Kg) at room temperature, filtered and dried to afford the sub-title compound (35.3 Kg, 83%) as a white solid. Decomposition pt 273° C. δ (DMSOd6): 7.93 (1H, d), 8.42 (1H, d). m/z (Found:220 [M+H]+, 100%. C6H6NO6S requires 220.17).

Workup

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

Sources & evidence

ORD record
ord-d328947a13654a91adc67f4f010f5638
Source dataset
uspto-grants-2006_02
Patent number
US07005520B2

Reaction notes

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