Sodium Hydroxide → (5-Methyl-1H-imidazol-4-yl)(quinolin-7-yl)methanone

HRID 1643391ノート

反応式

HRID 1643391 の反応式
[CH3:1][C:2]1[N:3]=[CH:4][N:5](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:6]=1[C:7]([C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)=[O:8].[OH-].[Na+]>C(O)(=O)C.O>[CH3:1][C:2]1[NH:3][CH:4]=[N:5][C:6]=1[C:7]([C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)=[O:8]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 66755765HCID 66755765、化合物

生成物 1

HCID 57965246(5-Methyl-1H-imidazol-4-yl)(quinolin-7-yl)methanone

試薬・触媒・溶媒 1

HCID 21899381Acetic acid--water (1/1)溶媒

実験手順

A solution of (8) in acetic acid/water (12 mL/8 mL) was heated at 110° C. for 1.5 h. The reaction was cooled to room temperature. Crushed ice was added, and basification of reaction with NaOH (s) to pH˜6 was followed. The aqueous layer was extracted with chloroform/isopropanol (3:1, 200 mL). The pooled organic layers were dried over magnesium sulfate. The mixture was filtered, and the solvents were removed under vacuum. The residue was purified by chromatography on silica gel with 3% saturated ammonia methanol in dichloromethane to give (5-methyl-1H-imidazol-4-yl)(quinolin-7-yl)methanone (9) as a white solid (0.53 g, 2.24 mmol, 35% over 3 steps).

後処理

  1. additionCrushed ice was added
  2. extractionThe aqueous layer was extracted with chloroform/isopropanol (3:1, 200 mL)
  3. dry with materialThe pooled organic layers were dried over magnesium sulfate
  4. filtrationThe mixture was filtered
  5. customthe solvents were removed under vacuum
  6. customThe residue was purified by chromatography on silica gel with 3% saturated ammonia methanol in dichloromethane

出典と根拠

ORDレコード
ord-cbae4f6faf7543488887f88093e5c72d
出典データセット
uspto-grants-2012_02
特許番号
US08119807B2

反応ノート

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