Hydrochloric Acid → 3-(Formylamino)-3,4-dihydro-2(1H)quinolinone

HRID 1648306

Reaktionsgleichung

Reaktionsgleichung von HRID 1648306
[OH-].[Na+].[CH:3]([NH:5][C:6]1(C(OCC)=O)[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]1=[O:16])=[O:4].O.Cl>CO>[CH:3]([NH:5][CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]1=[O:16])=[O:4]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 19919309Ethyl 3-(formylamino)-1,2,3,4-tetrahydro-2-oxo-3-quinolinecarboxylate

Produkt 1

HCID 179327143-(Formylamino)-3,4-dihydro-2(1H)quinolinoneAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium hydroxide (50 mL of 4.0 N, 0.20 mol) was added to a stirred solution of ethyl 3-(formylamino)-1,2,3,4-tetrahydro-2-oxo-3-quinolinecarboxylate (11.3 g, 0.043 mol) in methanol (250 mL). After 30 minutes, a white precipitate appeared and, after 45 minutes water (50 mL) was added to the reaction. After refluxing overnight, hydrochloric acid (50 mL of 4.0 N, 0.20 mol) was added and the solvents were removed under reduced pressure. The residual solid was refluxed in ethanol (200 mL) for 1 hour, filtered to remove salt, and cooled to afford 6.8 g of product, mp 197°-200° C. Anal. Calc'd for C10H10N2O2 : C, 63.15; H, 5.30; N, 14.73. Found: C, 63.03; H, 5.37; N, 14.71.

Aufarbeitung

  1. waita white precipitate appeared and, after 45 minutes
  2. temperatureAfter refluxing overnight
  3. customthe solvents were removed under reduced pressure
  4. temperatureThe residual solid was refluxed in ethanol (200 mL) for 1 hour
  5. filtrationfiltered
  6. customto remove salt
  7. temperaturecooled

Quellen und Nachweise

ORD-Eintrag
ord-f794fc3745bf4307b14228c45cb6bf7b
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05436240

Verknüpfte Notizen

Wird geladen…