Glycerol → 8-Methylsulfonyl-5-quinolinecarboxylic acid

HRID 1385036ノート

反応式

HRID 1385036 の反応式
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]

参加物

6

反応物 4

HCID 753GlycerolHCID 1118Sulfuric AcidHCID 5238Sodium IodideHCID 227288903-Amino-4-methylsulfonylbenzoic acid

生成物 1

HCID 184030278-Methylsulfonyl-5-quinolinecarboxylic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
140 °C

実験手順

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.

後処理

  1. temperatureThe reaction temperature was then increased to 150° C
  2. temperatureWhile the mixture was heated to and
  3. customwere collected
  4. temperatureAfter cooling
  5. additiondiluted with a further 800 ml of water
  6. filtrationthe mixture was filtered
  7. customA precipitate was formed which
  8. filtrationwas filtered off with suction
  9. filtrationthe resulting precipitate was filtered off with suction
  10. washwashed with water
  11. customdried

出典と根拠

ORDレコード
ord-f9447a6fbeef4fa6853220dc7a782936
出典データセット
uspto-grants-2001_07
特許番号
US06262074B1

反応ノート

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