StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Dimethylformamide → 6-Hydroxy-2-oxo-1,2-dihydroquinoline-5-carbaldehyde

HRID 579468
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 579468
BrC1C(=O)[O:4][C:5]2[C:10]([C:11]=1C)=[CH:9][CH:8]=[C:7](O)[CH:6]=2.B(O)(O)O.[C:19]([O-:22])([O-])=O.[Na+].[Na+].[CH3:25][N:26]([CH:28]=[O:29])C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:4][C:5]1[CH:10]=[CH:11][C:25]2[NH:26][C:28](=[O:29])[CH:9]=[CH:8][C:7]=2[C:6]=1[CH:19]=[O:22]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 7628Boric AcidHCID 10340Sodium CarbonateHCID 53375453-Bromo-7-hydroxy-4-methylchromen-2-one

Produkt 1

HCID 866834296-Hydroxy-2-oxo-1,2-dihydroquinoline-5-carbaldehydeAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397
HCID 178418397, Verbindung
Katalysator

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Compound 1 (15 g, 46 mmol), the boric acid (8.7 g, 50.6 mmol), Pd(PPh3)4 (1.88 g, 2.3 mmol), Na2CO3 (12.1 g, 115 mmol) were added to DMF (250 mL). The reaction mixture was degassed with N2 for three times, and then heated to 90° C. for 16 h. After cooled to RT, the solvent was concentrated, the residue was dissolved in sat Na2CO3 (150 mL). The aqueous was washed with DCM (100 mL×4), and then acidified by con.HCl to pH to ˜4. The result precipitate was collected by filtration, triturated with hot EA (50 mL), afforded compound 2 (6.5 g, 42%) as yellow solid. 1HNMR (DMSO-d6, 400 MHz): δ 10.55 (s, 1H), 7.71 (d, J=4.0 Hz, 1H), 7.24 (s, 1H), 7.19 (d, J=4.0 Hz, 1H), 6.86 (s, 1H), 3.88 (s, 3H), 2.45 (s, 3H).

Aufarbeitung

  1. customThe reaction mixture was degassed with N2 for three times
  2. temperatureAfter cooled to RT
  3. concentrationthe solvent was concentrated
  4. dissolutionthe residue was dissolved in sat Na2CO3 (150 mL)
  5. washThe aqueous was washed with DCM (100 mL×4)
  6. filtrationThe result precipitate was collected by filtration
  7. customtriturated with hot EA (50 mL)

Quellen und Nachweise

ORD-Eintrag
ord-fd2c5cdf448a4fdaaf8662ae7684b07b
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09040714B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion