2-Oxocyclohexanecarbaldehyde → Dimethyl 5,6,7,8-tetrahydroquinoline-2,3-dicarboxylate

HRID 980544ノート

反応式

HRID 980544 の反応式
[NH2:1]/[C:2](=[CH:7]\[C:8]([O:10][CH3:11])=[O:9])/[C:3]([O:5][CH3:6])=[O:4].[CH:12]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C:15]1=O)=O>>[N:1]1[C:15]2[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=2[CH:12]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[C:2]=1[C:3]([O:5][CH3:6])=[O:4]

参加物

3

反応物 2

HCID 121975852-OxocyclohexanecarbaldehydeHCID 122471171,4-Dimethyl (2Z)-2-amino-2-butenedioate

生成物 1

HCID 13730698Dimethyl 5,6,7,8-tetrahydroquinoline-2,3-dicarboxylate収率 18.9%

反応条件

温度
150 °C

実験手順

A mixture of 10.04 g dimethyl aminofumarate and 8.0 g 2-formylcyclohexanone is heated at 150° C. under a reflux condenser for one hour. The condenser is removed, and the volatile components allowed to escape. Material volatile at 0.5 mm and 150° C. is then removed. The residue is purified by flash chromatography on silica gel using hexane-ethyl acetate (4:1) as eluant. Fractions containing the product are combined to give 2.97 g dimethyl 5,6,7,8-tetrahydroquinoline-2,3-dicarboxylate as an amber oil having the appropriate NMR and IR spectra.

後処理

  1. customThe condenser is removed
  2. customMaterial volatile at 0.5 mm and 150° C. is then removed
  3. customThe residue is purified by flash chromatography on silica gel
  4. additionFractions containing the product

出典と根拠

ORDレコード
ord-e509f8e629c54c8bb64e699da536ab5c
出典データセット
uspto-grants-1987_01
特許番号
US04638068

反応ノート

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