Dimethylformamide → 2-Methyl-8-(2-oxopropoxy)quinoline

HRID 263970

Reaktionsgleichung

Reaktionsgleichung von HRID 263970
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Cl[CH2:25][C:26](=[O:28])[CH3:27]>C1COCC1>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([O:12][CH2:25][C:26](=[O:28])[CH3:27])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 132242-Methyl-8-hydroxyquinoline

Produkt 1

HCID 107274142-Methyl-8-(2-oxopropoxy)quinolineAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Methyl-8-hydroxyquinoline (0.80 g, 5 mmol), potassium carbonate (0.69 g, 5 mmol) and dry N,N-dimethylformamide (DMF) (40 ml) were stirred at room temperature for 30 min. To this solution was added chloroacetone (0.46 g, 5 mmol) in dry THF (10 ml) in one portion. The resulting mixture was stirred at room temperature for 24 h. (monitored by TLC) and then poured into ice water (100 ml). The pale yellow solid thus obtained was collected and crystallized from dichloromethane and ether to afford 2-methyl-8-(2-oxopropoxy)quinoline (10a) (0.77 g, 72%). mp: 99°-100° C.; 1H-NMR (CDCl3): δ2.35 (s, 3H, 2'-CH3), 2.79 (s, 3H, 2-CH3), 4.86 (s, 2H, OCH2), 6.88-7.44 (m, 3H, Ar--H), 7.33 (d, 1H, 3-H), 8.03 (d, 1H, 4-H).

Aufarbeitung

  1. customThe pale yellow solid thus obtained
  2. customwas collected
  3. customcrystallized from dichloromethane and ether

Quellen und Nachweise

ORD-Eintrag
ord-f8fb5c390c78407f9107861dd3f4029d
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646164

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