N-bromobutanimide → Ethyl 2-bromomethyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate

HRID 1722786Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1722786
[CH3:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[CH:5]=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:3]=1.[Br:28]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:28][CH2:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[CH:5]=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:3]=1

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 10248079Ethyl 2-methyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate

Produkt 1

HCID 10388561Ethyl 2-bromomethyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylateAusbeute 32,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of ethyl 2-methyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate (5 g), N-bromosuccinimide (5.9 g) and benzoyl peroxide (0.1 g) in carbon tetrachloride (200 ml) was refluxed for 5 hours. The reaction mixture was poured into ice water (100 ml). The separated organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride successively, dried over magnesium sulfate and evaporated in vacuo. The residue was subjected to a column chromatography on silica gel eluting with a mixture of n-hexane and chloroform (1:2 V/V). The fractions containing the desired compound were combined and evaporated in vacuo to give ethyl 2-bromomethyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate (2 g).

Aufarbeitung

  1. temperaturewas refluxed for 5 hours
  2. washThe separated organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride successively
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. additionThe residue was subjected to a column chromatography on silica gel eluting with a mixture of n-hexane and chloroform (1:2 V/V)
  6. additionThe fractions containing the desired compound
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9dea3bc11b7d4762a89a638855169b00
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04857527

Notizen zur Reaktion

Wird geladen…