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

HRID 1740629

반응식

HRID 1740629 반응식
[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

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 887Methanol2회HCID 4311764Sodium borohydride2회HCID 220074481-[2-(2-Oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7ea7aa0637b34dd496838da4db3694fd
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05969140

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