2-Bromoanisole → N-[alpha-(2-methoxyphenyl)benzyl]-4-pyridinamine

HRID 1448602Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1448602
[CH:1](=[N:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Li].BrC1C=CC=CC=1OC>CCOCC.CCCCCC>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH:1]([NH:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 113582-BromoanisoleHCID 6428664-BenzylideneaminopyridineHCID 178506687HCID 178506687, Verbindung

Produkt 1

HCID 20380334N-[alpha-(2-methoxyphenyl)benzyl]-4-pyridinamineAusbeute 49,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

2.98 Grams (0.016 mole) of 4-benzylideneaminopyridine in 50 milliliters of dry ether were added dropwise to a stirred solution of 2-methoxyphenyl lithium (prepared from 0.03 mole of butyl lithium and 5.61 grams [0.03 mole] of o-bromoanisole) in a mixture of ether and hexane at 0° C. under nitrogen. The mixture was stirred at room temperature for 2 hours and then poured onto ice. The organic layer was separated and extracted with acid and the acid extracts were combined with the aqueous layer. The combined aqueous medium was basified with 5 N sodium hydroxide and extracted into dichloromethane. After drying over magnesium sulphate, the solvent was removed to leave a solid which yielded 2.3 grams of title compound, m.p. 143°-5° C. The product was converted into its hydrobromide salt, m.p. 196°-198° C., by solution in 2-propanol and addition of hydrogen bromide in dry ether.

Aufarbeitung

  1. additionpoured onto ice
  2. customThe organic layer was separated
  3. extractionextracted with acid
  4. extractionextracted into dichloromethane
  5. dry with materialAfter drying over magnesium sulphate
  6. customthe solvent was removed
  7. customto leave a solid which

Quellen und Nachweise

ORD-Eintrag
ord-4796d75f1cce4192b121dd1c25867d30
Quelldatensatz
uspto-grants-1979_12
Patentnummer
US04180670

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