Sodium Hydroxide → HCID 58492441、化合物

HRID 1874063ノート

反応式

HRID 1874063 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 58492441HCID 58492441、化合物収率 103.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-7e0384a12e5641588fbb866b99b01b99
出典データセット
uspto-grants-2012_11
特許番号
US08304546B2

反応ノート

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