Sodium Hydroxide → HCID 58492441, 화합물

HRID 68170노트

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HRID 68170 반응식
[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:28])[C:5]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[C:6]([C:16](OC)=[O:17])[NH:7]2.[OH-].[Na+]>ClCCl>[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:28])[C:5]([C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)=[C:6]([CH2:16][OH:17])[NH:7]2

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 58492499Methyl 5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydroquinoline-2-carboxylate

생성물 1

HCID 58492441HCID 58492441, 화합물수율 103.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A dichloromethane solution (30 ml) of methyl 5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydroquinoline-2-carboxylate (5.0 g, 13 mmol) was cooled to −78° C., and hydrogenated diisobutylaluminium (DIBAL-H, 1M toluene solution, 30 ml) was added thereto dropwise under a nitrogen atmosphere. After completion of the addition, the mixture was stirred at the same temperature for 3 hours. The reaction mixture was heated to room temperature, and 5N sodium hydroxide was added thereto, followed by extraction with dichloromethane. The thus-obtained organic layer was washed with water, dried over sodium sulfate, and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:methanol=10:1). The purified material was concentrated to dryness under reduced pressure, giving a yellow amorphous solid of 5-fluoro-2-hydroxymethyl-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one (4.8 g, yield: 85%).

후처리

  1. additionAfter completion of the addition
  2. extractionfollowed by extraction with dichloromethane
  3. washThe thus-obtained organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified
  7. concentrationThe purified material was concentrated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-c1a7f788d15c40fa84e0ba2f4ea69c2e
출처 데이터셋
uspto-grants-2014_09
특허 번호
USRE045108E1

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