Aniline → N-phenyl-3-methyl-2-pyridinecarboxamide

HRID 2351569Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2351569
[CH3:1][C:2]1[C:3]([C:8]([NH2:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.B(F)(F)F.CCOCC.O1CCCC1.N[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O>[C:26]1([NH:10][C:8]([C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=2)=[O:9])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

6

Edukt 4

HCID 6115AnilineHCID 8000Boron trifluoride etherateHCID 8028TetrahydrofuranHCID 166410233-Methylpyridine-2-carboxamide

Produkt 1

HCID 13115134N-phenyl-3-methyl-2-pyridinecarboxamideAusbeute 354,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To 3-methyl-2-pyridinecarboxamide (15.0 o, 0.11 mole) are added BF3.OEt2 (14.0 mL, 0.11 mole) and tetrahydrofuran (75 mL). After about 5 minutes, aniline (10.3 g, 0.11 mole) is slowly added and the solution is heated at reflux for 5 hours. The reaction is cooled and diluted with water and the oroduct is extracted into ethyl acetate. The solvent is removed and the residue is purified by silica gel chromatography to give 8.32 g (0.39 mole, 35%) of N-phenyl-3-methyl-2-pyridinecarboxamide.

Aufarbeitung

  1. temperaturethe solution is heated
  2. temperatureat reflux for 5 hours
  3. temperatureThe reaction is cooled
  4. extractionthe oroduct is extracted into ethyl acetate
  5. customThe solvent is removed
  6. customthe residue is purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f02a44f659274e69bf8aba5bfa649e16
Quelldatensatz
uspto-grants-1989_10
Patentnummer
US04873335

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