Hydrogen Peroxide → Methyl 3-hydroxyquinoline-8-carboxylate

HRID 1819769ノート

反応式

HRID 1819769 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[CH:10]2)=[O:4].OO.C([O-])(O)=[O:18].[Na+]>CC(O)=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][C:11]([OH:18])=[CH:10]2)=[O:4]

参加物

5

反応物 3

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 12554533Methyl Quinoline-8-Carboxylate

生成物 1

HCID 57440941Methyl 3-hydroxyquinoline-8-carboxylate収率 44%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
85 °C

実験手順

To the mixture of 8-quinoline carboxylic acid (500 mg, 2.89 mmol) in THF (80 mL) was added CH2N2 in Et2O sol. [Prepared from nitrosomethylurea (1.65 g) and 50% KOH (5 mL)] at room temperature. The reaction mixture was stirred for 12 h and then concentrated to give the intermediate ester. 1H NMR (300 MHz, DMSO-d6) δ 3.92 (3H, s), 7.60-7.70 (2H, m), 7.93-7.96 (1H, m), 8.14-8.17 (1H, m), 8.44-8.48 (1H, m), 8.97-8.99 (1H, m). To a solution of the intermediate 8-Quinolinecarboxylic acid methyl ester (2.89 mmol) in AcOH (4 mL) was added 30% H2O2 (0.6 mL). The reaction mixture was heated at 85° C. for 7.5 h. The reaction mixture was treated with sat NaHCO3, and extracted six times with CHCl3. Organic layer was dried over anhydrous MgSO4, and concentrated. Crude residue was triturated with CHCl3/toluene to provide compound 97 (256 mg, 44%, in 2 steps). 1H NMR (300 MHz, DMSO-d6) δ 3.89 (3H, s), 7.52 (1H, d, J=6.9 Hz), 7.57 (1H, d, J=1.5 Hz), 7.66 (1H, dd, J=1.5, 6.9 Hz), 7.95 (1H, dd, J=1.5, 8.1 Hz), 8.63 (1H, d, J=2.7 Hz), 10.5 (1H, br s).

後処理

  1. extractionextracted six times with CHCl3
  2. dry with materialOrganic layer was dried over anhydrous MgSO4
  3. concentrationconcentrated
  4. customCrude residue was triturated with CHCl3/toluene

出典と根拠

ORDレコード
ord-be082cb14f7248d096fc6395dd9a7a26
出典データセット
uspto-grants-2009_10
特許番号
US07601841B2

反応ノート

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