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

HRID 482241

Reaktionsgleichung

Reaktionsgleichung von HRID 482241
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-340761dca04a4b149339d73a99b3728d
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05795889

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