Hydrochloric Acid → 7-((5-Methyl-1H-imidazol-4-yl)methyl)quinoline

HRID 1643392ノート

反応式

HRID 1643392 の反応式
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=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.[OH-].[K+].O.NN.Cl>C(O)CO>[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 57965246(5-Methyl-1H-imidazol-4-yl)(quinolin-7-yl)methanone

生成物 1

HCID 249989787-((5-Methyl-1H-imidazol-4-yl)methyl)quinoline収率 65%

試薬・触媒・溶媒 1

HCID 174Ethylene Glycol溶媒

反応条件

温度
120 °C

実験手順

A mixture of (9) (0.53 g, 2.23 mmol), potassium hydroxide (0.50 g, 8.91 mol), and hydrazine hydrate (0.45 mL, 14.4 mmol) in ethylene glycol was heated at 120° C. for 1 h, then kept at 165° C. overnight. The reaction mixture was cooled to room temperature and acidified with 2 M HCl (aq) to pH˜4. The aqueous layer was washed with chloroform/isoprpanol (3:1, 200 ml). The aqueous layer was basified to pH˜7, and 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 7-((5-methyl-1H-imidazol-4-yl)methyl)quinoline (10) as a yellow foam (0.32 mg, 1.45 mmol, 65% yield).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe aqueous layer was washed with chloroform/isoprpanol (3:1, 200 ml)
  3. extractionextracted with chloroform/isopropanol (3:1, 200 mL)
  4. dry with materialThe pooled organic layers were dried over magnesium sulfate
  5. filtrationThe mixture was filtered
  6. customthe solvents were removed under vacuum
  7. 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-2ac26afc246141d1a8f6e1cad364c62e
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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