Methanol → HCID 15166991, compound

HRID 1195653Notes

Reaction equation

HRID 1195653 reaction equation
[C:1]([CH2:4][S:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:16]([O-:18])=[O:17])[CH:7]=1)(O)=O.[C:19]([O:23][CH3:24])(=[O:22])C=C.[CH3:25]O>C(N(C(C)C)C(C)C)C>[CH3:24][O:23][C:19]([CH2:1][CH2:4][S:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:16]([O:18][CH3:25])=[O:17])[CH:7]=1)=[O:22]

Participants

5

Reactant 3

HCID 887MethanolHCID 7294Methyl AcrylateHCID 86744866HCID 86744866, compound

Product 1

HCID 15166991HCID 15166991, compound

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

Methyl 4(lH)-thioquinolone-2-carboxylate (1.0 equivalent) from example 24 is suspended/dissolved in MeOH containing a catalytic amount of ethyldiisopropylamine. To this mixture is added methyl acrylate (3 equivalent) and the whole is refluxed for 3 hours. The bulk of the solvent is removed under vacuum and the residue is recrystallized from ethyl acetate/ hexane to give methyl 4-(2-methoxycarbonyl-ethylthio)-quinoline-2-carboxylate.

Workup

  1. temperaturethe whole is refluxed for 3 hours
  2. customThe bulk of the solvent is removed under vacuum
  3. customthe residue is recrystallized from ethyl acetate/ hexane

Sources & evidence

ORD record
ord-9298245b37bb4055a4e03d1b035203e6
Source dataset
uspto-grants-1992_05
Patent number
US05112821

Reaction notes

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