Glycerol → 8-Methylsulfonyl-5-quinolinecarboxylic acid
Reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[S:16]([CH3:19])(=[O:18])=[O:17])[C:10]([OH:12])=[O:11].[I-].[Na+].O[CH2:23][CH:24]([CH2:26]O)O>O>[CH3:19][S:16]([C:15]1[C:7]2[N:6]=[CH:26][CH:24]=[CH:23][C:8]=2[C:9]([C:10]([OH:12])=[O:11])=[CH:13][CH:14]=1)(=[O:18])=[O:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
38 ml of water and 102 g of concentrated sulfuric acid were heated to 110° C. At 95° C., 0.25 mol of 3-amino-4-methylsulfonylbenzoic acid was added. The mixture was then heated to 140° C., and 0.8 g of sodium iodide and 0.3 mol of glycerol were added. The reaction temperature was then increased to 150° C. While the mixture was heated to and stirred at 150° C. (1 hour), 47 g of distillate were collected. After cooling, the reaction mixture was carefully admixed with 200 ml of water and diluted with a further 800 ml of water. Using 20% strength aqueous sodium hydroxide solution, the pH was adjusted to 13 and the mixture was filtered and adjusted to pH 3.5 with sulfuric acid. This procedure was repeated. A precipitate was formed which was filtered off with suction. The filtrate was adjusted to pH=2 and the resulting precipitate was filtered off with suction, washed with water and dried.
Workup
- temperatureThe reaction temperature was then increased to 150° C
- temperatureWhile the mixture was heated to and
- customwere collected
- temperatureAfter cooling
- additiondiluted with a further 800 ml of water
- filtrationthe mixture was filtered
- customA precipitate was formed which
- filtrationwas filtered off with suction
- filtrationthe resulting precipitate was filtered off with suction
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-f9447a6fbeef4fa6853220dc7a782936
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06262074B1
Reaction notes
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