Sodium Bicarbonate → HCID 21824645、化合物

HRID 505226ノート

反応式

HRID 505226 の反応式
[Cl:1][C:2]1[CH:3]=[C:4](S(O)(=O)=O)[C:5]2[CH:6]=[CH:7][C:8]([CH3:13])=[N:9][C:10]=2[C:11]=1[OH:12].C([O-])(O)=O.[Na+]>C(O)(=O)C.S(=O)(=O)(O)O.O>[Cl:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:13])=[N:9]2)=[CH:4][CH:3]=1

参加物

6

反応物 2

HCID 516892Sodium BicarbonateHCID 21824655HCID 21824655、化合物

生成物 1

HCID 21824645HCID 21824645、化合物収率 82.3%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 1118Sulfuric Acid溶媒

実験手順

7-Chloro-8-hydroxy-2-methyl-quinoline-5-sulfonic acid (5.50 g, 20.09 mmol) was dissolved in acetic acid (30 ml) and sulfuric acid (3 ml), and the resulting solution was heated to 130° C. for 72 hours. Upon cooling, the reaction mixture was diluted with water (300 ml) and neutralized by the addition of solid NaHCO3. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified via flash chromatography (gradient of hexane/EtOAc 95:5 to 70:30) to afford the title compound (3.20 g, 82%) as a yellow solid. 1H NMR (400 MHz, d6-DMSO): δ=10.6-10.1 (br, 1H), 8.30 (d, J=7.7 Hz, 1H), 7.55-7.51 (m, 2H), 7.43 (d, J=8.8 Hz, 1H), 2.77 (s, 3H). MS (ES−): 192.2 (M−H)−.

後処理

  1. temperatureUpon cooling
  2. extractionThe aqueous phase was extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via flash chromatography (gradient of hexane/EtOAc 95:5 to 70:30)

出典と根拠

ORDレコード
ord-5c64b891e7294efbab0e28a44218a317
出典データセット
uspto-grants-2010_08
特許番号
US07781438B2

反応ノート

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