Pyruvic Acid → HCID 18788530, compound

HRID 374470Notes

Reaction equation

HRID 374470 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[C:8]([OH:13])(=[O:12])[C:9]([CH3:11])=O.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[NH2:19]>CCO>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[C:9]([C:8]([OH:13])=[O:12])[C:20]2[C:18](=[CH:17][C:16]([O:15][CH3:14])=[C:22]([O:23][CH3:24])[CH:21]=2)[N:19]=1

Participants

5

Reactant 3

HCID 1060Pyruvic AcidHCID 73642-ThiophenecarboxaldehydeHCID 227703,4-Dimethoxyaniline

Product 1

HCID 18788530HCID 18788530, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a boiling solution of 2-thiophenecarboxaldehyde (1.22 ml), pyruvic acid (0.904 ml) and 50 ml absolute EtOH is added dropwise a solution of 3,4-dimethoxyaniline (2.00 g) in 100 ml EtOH. The mixture is refluxed for approximately 4 hours, then stored at room temperature overnight. The greenish-yellow precipitate is collected by filtration, washed with fresh EtOH then with ether and allowed to air dry to obtain 2-(thien-2-yl)-4-carboxy-6,7-dimethoxyquinoline m.p. 260°-263° C.).

Workup

  1. temperatureThe mixture is refluxed for approximately 4 hours
  2. filtrationThe greenish-yellow precipitate is collected by filtration
  3. washwashed with fresh EtOH
  4. customto air dry

Sources & evidence

ORD record
ord-601599d1a63c4808abcd29c88cf973a5
Source dataset
uspto-grants-1996_01
Patent number
US05480883

Reaction notes

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