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

HRID 1650102Notes

Reaction equation

HRID 1650102 reaction equation
[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]

Participants

3

Reactant 2

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

Product 1

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

Conditions

Temperature
150 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-953038f0e9684e0fab561e8e414c4ac3
Source dataset
uspto-grants-1990_05
Patent number
US04923504

Reaction notes

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