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

HRID 535473노트

반응식

HRID 535473 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7a315499cb474984ac9005769d826a55
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859544B2

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