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

2-Bromopyridine → 4-Methoxy-2'-[hydroxy(2-pyridyl)methyl]benzanilide

HRID 1659241
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1659241
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[Li].BrC1C=CC=CN=1.C([Li])CCC.[CH3:20][O:21][C:22]1[CH:38]=[CH:37][C:25]([C:26]([NH:28][C:29]2[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=2[CH:31]=[O:32])=[O:27])=[CH:24][CH:23]=1>O1CCCC1.CCCCCC.CCOCC>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([NH:28][C:29]2[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=2[CH:31]([OH:32])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:27])=[CH:37][CH:38]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 79732-BromopyridineHCID 585595N-(2-Formylphenyl)-4-methoxybenzamideHCID 178418339ButyllithiumHCID 178506720HCID 178506720, Verbindung

Produkt 1

HCID 205600424-Methoxy-2'-[hydroxy(2-pyridyl)methyl]benzanilideAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283
Diethyl Ether
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

Pyridyl lithium, prepared by adding 2-bromopyridine (30.0 g., 0.19 mole) in 200 ml. of ether to 131 ml. of a hexane solution of 1.6 mole n-butyl lithium (0.2 mole) at -70° C., is added in 25 min. to a solution of o-(4-methoxybenzamido)benzaldehyde (8.9 g., 0.035 mole) in 300 ml. of tetrahydrofuran at -25° C. over a 20 min. period with stirring. Stirring is continued for 20 min. at -25° C. 1 hr. at -10° C. and then at 0° C. for 30 min. The reaction mixture is poured into 1500 ml. of cold 1 N hydrochloric acid, the aqueous layer separated, washed with ethyl acetate, made strongly basic with concentrated ammonium hydroxide and extracted with ethyl acetate. The ethyl acetate extract is washed with water, brine, dried over sodium sulfate and concentrated and the residue thus obtained triturated with ether to provide a 46% yield of 4-methoxy-2'-[hydroxy(2-pyridyl)methyl]benzanilide, m.p. 127.5°-128.5° C. (corr.).

Aufarbeitung

  1. custom1 hr
  2. waitat -10° C. and then at 0° C. for 30 min
  3. additionThe reaction mixture is poured into 1500 ml
  4. customof cold 1 N hydrochloric acid, the aqueous layer separated
  5. washwashed with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. extractionThe ethyl acetate extract
  8. washis washed with water, brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated
  11. customthe residue thus obtained
  12. customtriturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-c36e0c049ff34c5caba9906b34d318ed
Quelldatensatz
uspto-grants-1981_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
USRE030811

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion