Hydrochloric Acid → HCID 67770344、化合物

HRID 373775ノート

反応式

HRID 373775 の反応式
[Na].[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[Cl:13])[NH:9][C:8](=[O:14])[CH:7]=[N:6]2.Br[CH:16]([CH2:22][CH2:23][CH2:24][CH3:25])[C:17]([O:19][CH2:20][CH3:21])=[O:18].Cl>C(O)C>[CH2:20]([O:19][C:17]([CH2:16][CH2:22][CH2:23][CH2:24][CH2:25][N:9]1[C:10]2[C:5](=[CH:4][C:3]([Cl:2])=[C:12]([Cl:13])[CH:11]=2)[N:6]=[CH:7][C:8]1=[O:14])=[O:18])[CH3:21]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 79072Ethyl 2-bromohexanoateHCID 5360545SodiumHCID 144236366,7-Dichloroquinoxalin-2(1H)-one

生成物 1

HCID 67770344HCID 67770344、化合物収率 10.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Under a nitrogen atmosphere sodium (0.148 g, 6.42 mmol) was dissolved in 50 ml of abs. ethanol and 6,7-dichloroquinoxalin-2(1H)-one (1.20 g, 5.58 mmol) (Liebigs Ann. Chem., (1982), 754) was added. The mixture was stirred until the compound dissolved, and ethyl 2-bromohexanoate (1.30 ml, 7.1 mmol) was added. The reaction mixture was refluxed for 72 h, cooled to room temperature, then poured onto crushed ice and acidified by dilute hydrochloric acid (pH=2). The precipitated compound was extracted with ethyl acetate and purified by column chromatography on silica gel (eluent 15% THF in heptane) to afford 0,21 g of 1-((1-ethoxycarbonyl)pentyl)-6,7-dichloroquinoxalin-2(1H)-one 1H-NMR(DMSO-d6):δ 0.78(t, 3H), 1.1(t, 3H), 1.15-1.35(m, 4H), 2.0-2.25(m, 2H), 4.02-4.18(m, 2H), 5.58-5.75(m, 1H), 8.02-8.36(broad, 1H), 8.18(s, 1H), 8.33(s, 1H).

後処理

  1. dissolutiondissolved
  2. temperatureThe reaction mixture was refluxed for 72 h
  3. additionpoured
  4. customonto crushed ice
  5. extractionThe precipitated compound was extracted with ethyl acetate
  6. custompurified by column chromatography on silica gel (eluent 15% THF in heptane)

出典と根拠

ORDレコード
ord-6afe7c461ef34a2fa6c9a9c3277b3e9a
出典データセット
uspto-grants-1992_11
特許番号
US05166155

反応ノート

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