2-Methyl-8-hydroxyquinoline → 2-(Hydroxyiminomethyl)quinolin-8-ol

HRID 623399

反応式

HRID 623399 の反応式
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.OC1C=CC=C2C=1N=C(C=O)C=C2.CC([O-])=O.[Na+].Cl.[NH2:32][OH:33]>O1CCOCC1.O>[OH:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH:1]=[N:32][OH:33])[CH:11]=[CH:10]2

参加物

7

反応物 4

HCID 132242-Methyl-8-hydroxyquinolineHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 5993428-Hydroxy-2-quinolinecarboxaldehyde

生成物 1

HCID 6047332-(Hydroxyiminomethyl)quinolin-8-ol

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
80 °C

実験手順

A solution of 2-methyl-quinolin-8-ol (536 mg, 3.37 mmol) in dioxane (8 mL) was added dropwise over 3 h into a stirred mixture of SeO2 (665 mg, 5.99 mmol) in dioxane (25 mL) at 50-55° C. The resulting mixture was then heated at 80° C. for 16 h, cooled, and the solids filtered off. The filtrate was concentrated and the residue purified by column chromatography on silica (dichloromethane/MeOH, 1:0-40:1). This afforded 8-hydroxy-quinoline-2-carboxaldehyde 4 as a straw-coloured solid (358 mg, 61%). 4: 1H NMR (CDCl3): δ 10.24 (s, 1H), 8.34 (d, J=8.6, 1H), 8.22 (br, 1H), 8.07 (d, J=8.6, 1H), 7.64 (dd, J=7.5 and 8.0, 1H), 7.44 (d, J=8.0, 1H), 7.30 (d, J=7.5, 1H). The mixture of 4 (100 mg, 0.578 mmol), NaOAc (63 mg, mmol), hydroxylamine hydrochloride (60 mg, 0.863 mmol) and water (5 mL) was heated at 100° C. for 15 min. The precipitate was isolated by filtration. This provided the title oxime (ID 969) D1 as an off-white solid (87 mg, 80%); spectral data of this compound are shown in Table 2.

後処理

  1. temperaturecooled
  2. filtrationthe solids filtered off
  3. concentrationThe filtrate was concentrated
  4. customthe residue purified by column chromatography on silica (dichloromethane/MeOH, 1:0-40:1)
  5. temperaturewas heated at 100° C. for 15 min
  6. customThe precipitate was isolated by filtration

出典と根拠

ORDレコード
ord-75aab6ae20004150b700cec79767a5e5
出典データセット
uspto-grants-2016_04
特許番号
US09302993B2

関連ノート

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