Hydrochloric Acid → 1-cyclopropyl-9-methyl-8-(1-methylisoindoline-5-yl)-4-oxo-4H-quinolizine-3-carboxylic acid

HRID 1061438ノート

反応式

HRID 1061438 の反応式
C(O)C.Cl.[CH:5]1([C:8]2[CH:9]=[C:10]([C:30]([O:32]CC)=[O:31])[C:11](=[O:29])[N:12]3[C:17]=2[C:16]([CH3:18])=[C:15]([C:19]2[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=2)[CH:24]([CH3:28])[NH:23][CH2:22]4)[CH:14]=[CH:13]3)[CH2:7][CH2:6]1>C1COCC1>[CH:5]1([C:8]2[CH:9]=[C:10]([C:30]([OH:32])=[O:31])[C:11](=[O:29])[N:12]3[C:17]=2[C:16]([CH3:18])=[C:15]([C:19]2[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=2)[CH:24]([CH3:28])[NH:23][CH2:22]4)[CH:14]=[CH:13]3)[CH2:7][CH2:6]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 18629334ethyl 1-cyclopropyl-9-methyl-8-(1-methylisoindoline-5-yl)-4-oxo-4H-quinolizine-3-carboxylate

生成物 1

HCID 186293251-cyclopropyl-9-methyl-8-(1-methylisoindoline-5-yl)-4-oxo-4H-quinolizine-3-carboxylic acid収率 47.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

7.6 ml ethanol, 2.5 ml of THF and 1.3 ml of 1N hydrochloric acid were added to 312.5 mg of ethyl 1-cyclopropyl-9-methyl-8-(1-methylisoindoline-5-yl)-4-oxo-4H-quinolizine-3-carboxylate (XIV) and the resulting mixture was stirred at room temperature for 30 minutes. The solvent was distilled off under reduced pressure and water was added to the resulting residue and the resulting residue was washed with ethyl acetate, and thereafter, the resulting water layer was concentrated under reduced pressure. 10 ml of water, 5 ml of ethanol and 3 ml of 1N sodium hydroxide were added to the residue, which was stirred at 50° C. for 3 hours. The reaction solution was concentrated under reduced pressure, and thereafter, dissolved in 4 ml of water and neutralized with 1N hydrochloric acid. The precipitated crystal was separated by filtering to obtain 139.1 mg of 1-cyclopropyl-9-methyl-8-(1-methylisoindoline-5-yl)-4-oxo-4H-quinolizine-3-carboxylic acid.

後処理

  1. distillationThe solvent was distilled off under reduced pressure and water
  2. additionwas added to the resulting residue
  3. washthe resulting residue was washed with ethyl acetate
  4. concentrationthe resulting water layer was concentrated under reduced pressure
  5. addition10 ml of water, 5 ml of ethanol and 3 ml of 1N sodium hydroxide were added to the residue, which
  6. stirringwas stirred at 50° C. for 3 hours
  7. concentrationThe reaction solution was concentrated under reduced pressure
  8. dissolutiondissolved in 4 ml of water and neutralized with 1N hydrochloric acid
  9. customThe precipitated crystal was separated
  10. filtrationby filtering

出典と根拠

ORDレコード
ord-ea370e1b91e648cc93528d451eaa5a72
出典データセット
uspto-grants-2003_02
特許番号
US06525066B2

反応ノート

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