Benzyl Bromide → 3-Benzyloxy-6,7-dimethoxy-quinoline

HRID 482245

反応式

HRID 482245 の反応式
[OH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[C:7]([O:14][CH3:15])[CH:6]=2.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[H-].[Na+].CN1CCCN(C)C1=O>C1COCC1>[CH2:16]([O:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[C:7]([O:14][CH3:15])[CH:6]=2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

6

反応物 4

HCID 7498Benzyl BromideHCID 24758Sodium hydride2 回HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 100587666,7-Dimethoxyquinolin-3-ol

生成物 1

HCID 100858633-Benzyloxy-6,7-dimethoxy-quinoline

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To 3-hydroxy-6,7-dimethoxyquinoline (150 mg; 0.73 mmol) in 3 mL THF is added benzyl bromide (0.13 mL; 188 mg; 1.10 mmol) and NaH (59 mg; 1.46 mmol). This is stirred at room temperature for 1 hour and 25 mg of NaH added followed by 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone (DMPU) (255 mg; 2.07 mmol) and stirred at room temperature for 31/2 hours. The reaction mixture is partitioned between EtOAc and distilled H2O and extracted 2× with EtOAc. The latter is washed with brine, dried (MgSO4), filtered, evaporated to dryness and chromatographed with 1% MeOH/CHCl3 to obtain 3-benzyloxy-6,7-dimethoxyquinoline m.p. 146.5°-148.5° C.).

後処理

  1. stirringstirred at room temperature for 31/2 hours
  2. customThe reaction mixture is partitioned between EtOAc
  3. distillationdistilled H2O
  4. extractionextracted 2× with EtOAc
  5. washThe latter is washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customchromatographed with 1% MeOH/CHCl3

出典と根拠

ORDレコード
ord-5edbacb9a58941fc899bdf83916ca751
出典データセット
uspto-grants-1998_08
特許番号
US05795889

関連ノート

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