Hydrochloric Acid → 1-[2-(2-Oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene

HRID 613009

反応式

HRID 613009 の反応式
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:12]1[CH:17]=[C:16]([C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=3)[CH:21]=[C:20]([C:32](OC)=[O:33])[C:19]=2[C:36](OC)=[O:37])[CH:15]=[CH:14][N:13]=1.[BH4-].[Na+].CO.Cl>O1CCCC1.C(Cl)Cl>[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:12]1[CH:17]=[C:16]([C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=3)[CH:21]=[C:20]([CH2:32][OH:33])[C:19]=2[CH2:36][OH:37])[CH:15]=[CH:14][N:13]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 887Methanol2 回HCID 4311764Sodium borohydride2 回HCID 220074481-[2-(2-Oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene

生成物 1

HCID 99124671-[2-(2-Oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene収率 50.4%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 1-[2-(2-oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene (200 mg) in tetrahydrofuran is added sodium borohydride (36 mg), and the mixture is refluxed. To the mixture is added methanol (0.3 ml) under reflux over a period of one hour. The mixture is cooled to room temperature, and thereto is added sodium borohydride (36 mg). To the mixture is added methanol (0.3 ml) under reflux over a period of one hour. After the reaction is complete, methylene chloride and diluted hydrochloric acid are added to the mixture. The methylene chloride layer is separated, washed, dried and concentrated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform:methanol=20:1) to give 1-[2-(2-oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene (90 mg), which is listed in Table 6.

後処理

  1. temperaturethe mixture is refluxed
  2. temperatureunder reflux over a period of one hour
  3. temperatureunder reflux over a period of one hour
  4. customThe methylene chloride layer is separated
  5. washwashed
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto remove the solvent
  9. customThe residue is purified by silica gel column chromatography (solvent; chloroform:methanol=20:1)

出典と根拠

ORDレコード
ord-c87bcfed50f44b9bb0cc38c47dd40454
出典データセット
uspto-grants-1999_12
特許番号
US06005106

関連ノート

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