1,4-Dioxane → Methyl 3-fluoro-11-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[b]quinoline-1-carboxylate

HRID 521413ノート

反応式

HRID 521413 の反応式
O=[C:2]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:9]([O:11]C)=O.[NH2:13][C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([F:24])[CH:23]=1)[C:17]([O:19][CH3:20])=[O:18].O1CCOCC1>O>[F:24][C:22]1[CH:21]=[C:16]([C:17]([O:19][CH3:20])=[O:18])[C:15]2[C:9](=[O:11])[C:3]3[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:2]=3[NH:13][C:14]=2[CH:23]=1

参加物

5

反応物 3

HCID 312751,4-DioxaneHCID 288225Methyl 2-oxocycloheptane-1-carboxylateHCID 3807862Methyl 3-amino-5-fluorobenzoate

生成物 1

HCID 89669535Methyl 3-fluoro-11-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[b]quinoline-1-carboxylate収率 107.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
130 °C

実験手順

A mixture of methyl 2-oxocycloheptanecarboxylate (0.34 g, 2 mmol), methyl 3-amino-5-fluorobenzoate (0.33 g, 2 mmol), polyphosphoric acid (4.0 g) and dioxane (5 mL) was heated at 130° C. for 5 hours. After cooling to room temperature, the solution was diluted with water (100 mL), and NaOAc.3H2O (7.3 g) was added. Then the resulting precipitate was collected by filtration and dried. The solid was suspended in methanol (20 mL) and SOCl2 (10 mL) was added, the mixture was stirred at reflux for 5 hours, concentrated and treated with water (50 mL), extracted with ethyl acetate (3×50 mL). The organic layer was separated, concentrated and the residue was chromatographed to give the crude product (0.62 g). MS (ESI) m/e [M+1]+290.0.

後処理

  1. temperatureAfter cooling to room temperature
  2. additionwas added
  3. filtrationThen the resulting precipitate was collected by filtration
  4. customdried
  5. additionSOCl2 (10 mL) was added
  6. temperatureat reflux for 5 hours
  7. concentrationconcentrated
  8. additiontreated with water (50 mL)
  9. extractionextracted with ethyl acetate (3×50 mL)
  10. customThe organic layer was separated
  11. concentrationconcentrated
  12. customthe residue was chromatographed

出典と根拠

ORDレコード
ord-a937d8b4fc3f45eb803ae03ae362bce1
出典データセット
uspto-grants-2016_05
特許番号
US09328111B2

反応ノート

読み込み中…