Phosphorus oxychloride → Methyl 2-chloroquinoline-6-carboxylate

HRID 2080145ノート

反応式

HRID 2080145 の反応式
P(Cl)(Cl)([Cl:3])=O.[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N+:16]([O-])=[CH:15][CH:14]=[CH:13]2)=[O:9]>C(OCC)(=O)C>[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([Cl:3])[CH:14]=[CH:13]2)=[O:9]

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 21707072Methyl quinoline-6-carboxylate 1-oxide

生成物 1

HCID 56924381Methyl 2-chloroquinoline-6-carboxylate収率 28%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Phosphorus oxychloride (10 mL) was added to quinoline-6-carboxylic acid methyl ester N-oxide (1.5 g, 7.6 mmol), and the solution was refluxed for 2 hours. The reaction solution was poured onto an ice, and warmed gradually to room temperature. Ethyl acetate was added to the reaction solution, which was then extracted, and sequentially washed with an aqueous solution of saturated sodium bicarbonate and brine. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1), and the title compound (0.47 g, 2.1 mmol, 28%) was obtained as a white solid.

後処理

  1. temperaturethe solution was refluxed for 2 hours
  2. extractionwas then extracted
  3. washsequentially washed with an aqueous solution of saturated sodium bicarbonate and brine
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-5c7e6d15a87a4e569ee274eece6fa371
出典データセット
uspto-grants-2011_04
特許番号
US07932272B2

反応ノート

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