Acetic Acid → HCID 178474467, Verbindung

HRID 1651054

Reaktionsgleichung

Reaktionsgleichung von HRID 1651054
[C:1]([NH:4][C:5]1[N:6]=[C:7]([OH:29])[C:8]2[CH:14]=[C:13]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([O:25]C(=O)C)=[O:24])=[CH:19][CH:18]=3)[CH:12]=[N:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2].[OH-].[Na+].C(O)(=O)C>O>[C:1]([NH:4][C:5]1[N:6]=[C:7]([OH:29])[C:8]2[CH:14]=[C:13]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19][CH:18]=3)[CH:12]=[N:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 178474468HCID 178474468, Verbindung

Produkt 1

HCID 178474467HCID 178474467, VerbindungAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a suspension of 0.95 g of 2-acetamido-4- hydroxy-6-[2-(4-acetoxycarbonylphenyl)ethenyl]pyrido[2,3-d]pyrimidine in 50 mL of water was added 1N aqueous sodium hydroxide until a homogenous solution was obtained. Acidification with acetic acid resulted in the formation of a yellow precipitate which was collected by filtration. The filter cake was washed sequentially with water, methanol, acetone and ether. The residual solid was recrystallized from DMF to give 0.65 g (77%) of 2-acetamido-4-hydroxy-6-[2-(4-carboxyphenyl)-ethenyl]pyrido[2,3-d]pyrimidine, as a microcrystalline yellow solid, mp>300° C.; NMR (TFA-d ) delta 2.5 (s, 3H), 6.85, 7.32 (AB q, 2H, J=12 Hz), 7.45, 8.18 (AB q, 4H, J=9 Hz), 8.65 (s, 1H), 9.02 (s, 1H); IR (Nujol) 3300-2200 (br), 1685, 1655, 1630, 1600, 1565 cm-1. MS: Calc'd. for C 18 H14N4O4 : 350. Found: m/e 350 (base), 308

Aufarbeitung

  1. customwas obtained
  2. filtrationwas collected by filtration
  3. washThe filter cake was washed sequentially with water, methanol, acetone and ether
  4. customThe residual solid was recrystallized from DMF

Quellen und Nachweise

ORD-Eintrag
ord-c1f5350ef8f04e10be86cca0e0b0f609
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04927828

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