Pyruvic Acid → 2-(N-phenylsulfonylindol-3-yl)-4-carboxy-6,7-dimethoxyquinoline

HRID 263948

Reaction equation

HRID 263948 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=O.[C:7]1([S:13]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([CH:25]=O)=[CH:17]2)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[NH2:32]>CCO>[C:7]1([S:13]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([C:25]3[CH:4]=[C:2]([C:1]([OH:6])=[O:5])[C:33]4[C:31](=[CH:30][C:29]([O:28][CH3:27])=[C:35]([O:36][CH3:37])[CH:34]=4)[N:32]=3)=[CH:17]2)(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 1060Pyruvic AcidHCID 227703,4-DimethoxyanilineHCID 3633341-(Phenylsulfonyl)-3-indolecarboxaldehyde

Product 1

HCID 187886132-(N-phenylsulfonylindol-3-yl)-4-carboxy-6,7-dimethoxyquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Pyruvic acid (0.486 ml) is added to a suspension of (2.00 g) of N-phenylsulfonyl-3-indolecarboxaldehyde in 100 ml absolute EtOH. The mixture is heated to reflux and a solution of 3,4-dimethoxyaniline (1.074 g) in 50 ml absolute EtOH is added dropwise. The reaction is then refluxed for approximately three hours and stirred at RT for 72 hours. The yellow precipitate is collected by filtration, washed with EtOH then with ether and the solid collected. This is triturated with EtOAC/EtOH and dried and used directly in the next step.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. temperatureThe reaction is then refluxed for approximately three hours
  4. filtrationThe yellow precipitate is collected by filtration
  5. washwashed with EtOH
  6. customwith ether and the solid collected
  7. customThis is triturated with EtOAC/EtOH
  8. customdried

Sources & evidence

ORD record
ord-45630c572692454bb15966d2992d7478
Source dataset
uspto-grants-1997_07
Patent number
US05646153

Linked notes

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