8-Methyl-2-phenylquinoline-3-carboxaldehyde → HCID 67197756, Verbindung

HRID 1948728

Reaktionsgleichung

Reaktionsgleichung von HRID 1948728
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([CH:18]=[O:19])=[CH:7]2.[CH3:20][Li]>C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:8]([CH:18]([OH:19])[CH3:20])=[CH:7]2

Komponenten

4

Edukt 2

HCID 8336808-Methyl-2-phenylquinoline-3-carboxaldehydeHCID 178418348HCID 178418348, Verbindung2×

Produkt 1

HCID 67197756HCID 67197756, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 8-methyl-2-phenylquinoline-3-carboxaldehyde (211 mg, 0.85 mmol) in THF (6 mL) cooled to −78° C. was added methyllithium (1.6N solution in ether, 0.6 mL, 0.93 mmol). After 1 h a further portion of methyllithium (0.2 mL, 0.32 mmol) was added. The reaction was allowed to warm to r.t. before being quenched with water (10 mL). The THF was removed in vacuo and the residue partitioned between DCM (100 mL) and water (30 mL). The organic layer was separated, dried (MgSO4) and concentrated in vacuo. Purification by column chromatography (SiO2, 5-25% EtOAc in heptane) gave the title compound as a white solid (145 mg, 65%). δH (CDCl3) 8.42 (s, 1H), 7.70 (d, J 12 Hz, 1H), 7.60-7.63 (m, 2H), 7.42-7.55 (m, 5H), 5.23-5.31 (m, 1H), 2.80 (s, 3H), 1.87 (d, J 3.6 Hz, 1H), 1.47 (d, J 6.4 Hz, 3H). LCMS (ES+) 264.16 (M+H)+, RT 4.03 minutes (Method 4).

Aufarbeitung

  1. custombefore being quenched with water (10 mL)
  2. customThe THF was removed in vacuo
  3. customthe residue partitioned between DCM (100 mL) and water (30 mL)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography (SiO2, 5-25% EtOAc in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-28319f5592994a859bd5d9a8b0630a8e
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399483B2

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