2-Methyl-8-hydroxyquinoline → 8-hydroxy-2-methyl-quinoline-5-sulfonic Acid

HRID 505228Notes

Reaction equation

HRID 505228 reaction equation
[OH:1][S:2]([OH:5])(=O)=[O:3].O=S(=O)=O.[CH3:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[C:14]([OH:21])[CH:15]=[CH:16][CH:17]=2)[N:12]=1>S(=O)(=O)(O)O.CC(C)=O>[OH:21][C:14]1[C:13]2[N:12]=[C:11]([CH3:10])[CH:20]=[CH:19][C:18]=2[C:17]([S:2]([OH:5])(=[O:3])=[O:1])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 132242-Methyl-8-hydroxyquinolineHCID 24681Fuming sulfuric acid

Product 1

HCID 17122768-hydroxy-2-methyl-quinoline-5-sulfonic AcidYield 94%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
65 °C

Procedure

Oleum (18-24% SO3, 20 ml) was added to a solution of 2-methyl-quinolin-8-ol (10 g, 62.8 mmol) in concentrated sulfuric acid (40 ml). After warming to 65° C. for 2 hours, the reaction mixture was poured onto 200 g of crushed ice. The suspension was diluted with acetone (60 ml) and stirred for 10 minutes, whereupon solids were filtered off. After washing with acetone (3×60 ml) and drying under high vacuum, the title compound (14.13 g, 94%) was obtained as a slightly yellowish solid. 1H NMR (400 MHz, d6-DMSO): δ=9.60 (d, J=8.3 Hz, 1H), 8.02-7.94 (m, 2H), 7.29 (d, J=7.7 Hz, 1H), 2.94 (s, 3H). MS (ES+): 240.2 (M+H)+.

Workup

  1. filtrationwere filtered off
  2. washAfter washing with acetone (3×60 ml)
  3. customdrying under high vacuum

Sources & evidence

ORD record
ord-c01fcc17b6cc4175aa16271a4614bbef
Source dataset
uspto-grants-2010_08
Patent number
US07781438B2

Reaction notes

Loading…