Methanol → HCID 54509567, Verbindung

HRID 2209464

Reaktionsgleichung

Reaktionsgleichung von HRID 2209464
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[CH:4][C:3]=1Br.[N+:16]([C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1)([O-:18])=[O:17].CO.C([O-])([O-])=O.[Na+].[Na+]>[Al].C(OCC)(=O)C.CCCCCC.C1C=CC=CC=1>[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:23]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:16]([O-:18])=[O:17])[CH:24]=1

Komponenten

9

Edukt 4

HCID 887MethanolHCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 218656452-bromo-4-(4-pyridinylmethyl)Benzenamine

Produkt 1

HCID 54509567HCID 54509567, VerbindungAusbeute 85,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 241BenzeneLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 5359268AluminumLösungsmittel

Versuchsvorschrift

4-(4-Amino-3-bromobenzyl)pyridine (1.0 gm), 3-nitrobenzene boronic acid (0.63 gm), palladium tetrakis triphenylphosphine (0.47 gm), methanol (6.5 mL), 2.0M Na2CO3 (1.9 mL) and benzene (32 mL) are combined in a reaction flask that is wrapped in aluminum foil (to prevent exposure of the reagents to light). The reaction mixture is heated to reflux for 6 hours. The progress of the reaction is monitored by thin-layer chromatography (9:1 hexane:ethyl acetate). When the starting material is converted, the reaction mixture is allowed to cool and the solvents are removed. Ethyl acetate is added to the residue, the resultant solution is filtered through a pad of Na2SO4, and concentrated. The product is isolated by preparative thin-layer chromatography (9:1 hexane:ethyl acetate) yielding 983 mg of 4-[4-amino-3-(3-nitrophenyl)benzyl]pyridine as an orange oil.

Aufarbeitung

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 6 hours
  3. temperatureto cool
  4. customthe solvents are removed
  5. additionEthyl acetate is added to the residue
  6. filtrationthe resultant solution is filtered through a pad of Na2SO4
  7. concentrationconcentrated
  8. customThe product is isolated by preparative thin-layer chromatography (9:1 hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-81a3102cb48e4c0b8237898f90eb372f
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05455252

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