Water → 2-(4-Methoxyphenyl)imidazo[1,2-a]pyridine

HRID 838936

Reaktionsgleichung

Reaktionsgleichung von HRID 838936
C(=O)(O)[O-].[Na+].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)=O.O>C(O)C>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]2[N:6]=[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][N:8]3[CH:14]=2)=[CH:18][CH:19]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 104392-AminopyridineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 6949632-(4-Methoxyphenyl)imidazo[1,2-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 25.2 g. of sodium bicarbonate, 12.3 g. of 2-aminopyridine and 30 g. of α-bromo-p-methoxyacetophenone in 100 ml. of water and 550 ml. of absolute ethanol is heated at reflux temperatures for 1.5 hrs. The reaction mixture is concentrated under reduced pressure to a yellow solid, which is partitioned between chloroform and water. The organic layer is separated, dried over sodium sulfate. Removal of the chloroform in vacuo leaves the crude intermediate as a yellow solid. Recrystallization from ethanol-water gives 15.2 g. of the desired material, m.p. 131°-134° C.

Aufarbeitung

  1. additionA mixture of 25.2 g
  2. temperatureat reflux temperatures for 1.5 hrs
  3. concentrationThe reaction mixture is concentrated under reduced pressure to a yellow solid, which
  4. customis partitioned between chloroform and water
  5. customThe organic layer is separated
  6. dry with materialdried over sodium sulfate
  7. customRemoval of the chloroform in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5295dc35c0244cfc821b0c6616870d95
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04093616

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