Ammonium Hydroxide → Methyl 3-[3-(2-methyl-4,5-dihydro-1H-imidazol-1-yl)phenyl]isonicotinate

HRID 2234269

Reaktionsgleichung

Reaktionsgleichung von HRID 2234269
Cl[CH2:2][CH2:3][NH:4][C:5](=O)[CH3:6].P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:30]=[N:29][CH:28]=[CH:27][C:22]=2[C:23]([O:25][CH3:26])=[O:24])[CH:18]=[CH:19][CH:20]=1.[OH-].[NH4+]>C(OCC)(=O)C.ClCCl>[CH3:6][C:5]1[N:14]([C:15]2[CH:16]=[C:17]([C:21]3[CH:30]=[N:29][CH:28]=[CH:27][C:22]=3[C:23]([O:25][CH3:26])=[O:24])[CH:18]=[CH:19][CH:20]=2)[CH2:2][CH2:3][N:4]=1

Komponenten

7

Edukt 4

HCID 14923Ammonium HydroxideHCID 24819Phosphorus pentachlorideHCID 81815N-(2-Chloroethyl)acetamideHCID 11368161Methyl 3-(3-aminophenyl)isonicotinate

Produkt 1

HCID 11449306Methyl 3-[3-(2-methyl-4,5-dihydro-1H-imidazol-1-yl)phenyl]isonicotinateAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N-(2-chloroethyl)acetamide (0.32 g) in ethyl acetate (5 ml) was added over 10 min. to a stirred suspension of phosphorus pentachloride (0.55 g) in ethyl acetate (2 ml) at 0° C. under nitrogen to give a clear pale straw solution. After 45 min. at 0° C. a solution of methyl 3-(3-aminophenyl)isonicotinate (0.4 g) in dichloromethane (10 ml) was added over 15 min. at 0-5° C. The mixture was stirred at 0° C. for 10 min. and then allowed to warm up to 20° C. After 3 h the mixture was treated with ammonium hydroxide solution (28%, 5 ml) over 10 min. and stirring continued for ca. 1 h. The layers were allowed to separate, the organic layer was collected, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (dichloromethane:methanol:ammonia=100:10:1, v/v/v) to give 0.25 g (48%) of yellow oil.

Aufarbeitung

  1. customto give a clear pale straw solution
  2. temperatureto warm up to 20° C
  3. stirringstirring
  4. waitcontinued for ca. 1 h
  5. customto separate
  6. customthe organic layer was collected
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (dichloromethane:methanol:ammonia=100:10:1, v/v/v)

Quellen und Nachweise

ORD-Eintrag
ord-2a6bbe9d81fd4420a446cba485e33cea
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709677B2

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