Sodium Hydroxide → 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one

HRID 577477ノート

反応式

HRID 577477 の反応式
C(N(CC)C(=O)[O:5][C:6]1[C:15]([Cl:16])=[C:14]2[C:9]([CH2:10][CH2:11][N:12]([CH2:18][C:19]3[C:20]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[N:21][C:22]([CH3:26])=[CH:23][C:24]=3[CH3:25])[C:13]2=[O:17])=[CH:8][CH:7]=1)C.[OH-].[Na+]>CCO>[CH2:28]([O:27][C:20]1[C:19]([CH2:18][N:12]2[CH2:11][CH2:10][C:9]3[C:14](=[C:15]([Cl:16])[C:6]([OH:5])=[CH:7][CH:8]=3)[C:13]2=[O:17])=[C:24]([CH3:25])[CH:23]=[C:22]([CH3:26])[N:21]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 867237032-{[2-(Benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-1-oxo-1,2,3,4-tetrahydroisoquinolin-7-yl diethylcarbamate

生成物 1

HCID 867237042-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one収率 87%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-1-oxo-1,2,3,4-tetrahydroisoquinolin-7-yl diethylcarbamate (1g, 14.0 g, 26.8 mmol) and NaOH (10.7 g, 268 mmol) in EtOH (200 mL) was refluxed overnight. The reaction mixture was concentrated under vacuum. To the reaction mixture was added H2O (200 mL) and the solution was acidified with 1 N HCl to pH 3. The reaction mixture was extracted with EtOAc (2×200 mL). The combined organic layers were washed with brine (300 mL), dried over Na2SO4 and concentrated under vacuum. To the residue was added EtOAc (20 mL) and petroleum ether (100 mL). The mixture was filtered and the solids were dried under vacuum to give 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one (1 h, 9.8 g, 87%) as an off-white solid.

後処理

  1. temperaturewas refluxed overnight
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. additionTo the reaction mixture was added H2O (200 mL)
  4. extractionThe reaction mixture was extracted with EtOAc (2×200 mL)
  5. washThe combined organic layers were washed with brine (300 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. additionTo the residue was added EtOAc (20 mL) and petroleum ether (100 mL)
  9. filtrationThe mixture was filtered
  10. customthe solids were dried under vacuum

出典と根拠

ORDレコード
ord-4b393e76631b49d7b5ccf3e4e2299690
出典データセット
uspto-grants-2015_05
特許番号
US09040515B2

反応ノート

読み込み中…