Hydrochloric Acid → 6-[(2-Methylindolizin-3-yl)carbonyl]-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 535473ノート

反応式

HRID 535473 の反応式
[OH-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]2[N:11]([C:12]=1[C:13]([C:15]1[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=1)[N:21]([CH3:25])[CH:20]=[C:19]([C:26]([O:28]CC)=[O:27])[C:18]3=[O:31])=[O:14])[CH:10]=[CH:9][CH:8]=[CH:7]2.C(O)(C)(C)C.Cl>O>[CH3:3][C:4]1[CH:5]=[C:6]2[N:11]([C:12]=1[C:13]([C:15]1[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=1)[N:21]([CH3:25])[CH:20]=[C:19]([C:26]([OH:28])=[O:27])[C:18]3=[O:31])=[O:14])[CH:10]=[CH:9][CH:8]=[CH:7]2

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 14798Sodium HydroxideHCID 66652940Ethyl 6-[(2-methylindolizin-3-yl)carbonyl]-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

生成物 1

HCID 666533896-[(2-Methylindolizin-3-yl)carbonyl]-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid収率 96.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

0.27 ml (3.22 mmol) of a 1N aqueous solution of sodium hydroxide is added, at ambient temperature, to 0.5 g (1.29 mmol) of ethyl 6-[(2-methylindolizin-3-yl)carbonyl]-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate in 9 ml of a mixture of t-butanol and water (1/1). The reaction medium is refluxed for 1 hour, acidified with a 1N aqueous solution of hydrochloric acid at ambient temperature, and then extracted with dichloromethane. The organic phase is washed with water, dried over sodium sulphate, and concentrated under reduced pressure. The residue obtained is rinsed with ether and then dried under reduced pressure at 50° C. 448 mg of a yellow solid are obtained.

後処理

  1. temperatureThe reaction medium is refluxed for 1 hour
  2. extractionextracted with dichloromethane
  3. washThe organic phase is washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. washis rinsed with ether
  8. customdried under reduced pressure at 50° C

出典と根拠

ORDレコード
ord-7a315499cb474984ac9005769d826a55
出典データセット
uspto-grants-2014_10
特許番号
US08859544B2

反応ノート

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