Selenious Acid → (7-Chloro-2-formyl-quinolin-8-yl)-acetic acid ethyl ester

HRID 505223

反応式

HRID 505223 の反応式
[Se](O)(O)=[O:2].[CH2:5]([O:7][C:8](=[O:22])[CH2:9][C:10]1[C:11]([Cl:21])=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[C:17]([CH3:20])[CH:16]=[CH:15]2)[CH3:6]>O1CCOCC1.O>[CH2:5]([O:7][C:8](=[O:22])[CH2:9][C:10]1[C:11]([Cl:21])=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[C:17]([CH:20]=[O:2])[CH:16]=[CH:15]2)[CH3:6]

参加物

5

反応物 2

HCID 1091Selenious Acid2 回HCID 66882026(7-Chloro-2-methyl-quinolin-8-yl)-acetic acid ethyl ester

生成物 1

HCID 86253926(7-Chloro-2-formyl-quinolin-8-yl)-acetic acid ethyl ester収率 77%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

Selenious acid (193 mg, 1.50 mmol, 1.1 equiv) was added to a solution of (7-chloro-2-methyl-quinolin-8-yl)-acetic acid ethyl ester in dioxane (12 ml). The reaction mixture was heated to 100° C. After 20 and 40 minutes, additional portions of selenious acid (88 mg each) were added, and heating was continued for a total of 90 minutes. After cooling, the reaction mixture was diluted with water, filtered, and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via flash chromatography (gradient of hexane/EtOAc 100:0 to 80:20) to afford the title compound (292 mg, 77%). 1H NMR (400 MHz, CDCl3): δ=10.18 (s, 1H), 8.31 (d, J=8.1 Hz, 1H), 8.04 (d, J=8.1 Hz, 1H), 7.82 (d, J=7.7 Hz, 1H), 7.71 (d, J=7.7 Hz, 1H), 4.61 (s, 2H), 4.22 (q, J=7.3 Hz, 2H), 1.28 (t, J=7.3 Hz, 3H). MS (ES+): 278.2 (M+H)+.

後処理

  1. temperatureheating
  2. customwas continued for a total of 90 minutes
  3. temperatureAfter cooling
  4. filtrationfiltered
  5. extractionextracted with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified via flash chromatography (gradient of hexane/EtOAc 100:0 to 80:20)

出典と根拠

ORDレコード
ord-3b03c3282f3e49b7a222d2843d5dbf6b
出典データセット
uspto-grants-2010_08
特許番号
US07781438B2

関連ノート

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