Diisopropylethylamine → HCID 18353658, Verbindung

HRID 430073

Reaktionsgleichung

Reaktionsgleichung von HRID 430073
Cl[C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:14][CH2:15][CH2:16][CH:17]([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20].C(N(C(C)C)CC)(C)C>>[CH2:19]([O:18][CH:17]([O:21][CH2:22][CH3:23])[CH2:16][CH2:15][NH:14][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[CH3:20]

Komponenten

4

Edukt 3

HCID 81531DiisopropylethylamineHCID 5210291-Amino-3,3-diethoxypropaneHCID 123691662-Chloro-4-methoxyquinoline

Produkt 1

HCID 18353658HCID 18353658, VerbindungAusbeute 12 %

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To 2-chloro-4-methoxyquinoline (0.576 g, 3 mmol) was added 1-amino-3,3-diethoxypropane (0.515 g, 3.5 mmol) and diisopropylethylamine (5 ml). The mixture was stirred under argon at 95° C. for 60 h. Volatile material was removed in vacuo and the residue partitioned between ethyl acetate and water. The ethyl acetate soluble material was purified by chromatography on silica gel eluting with 0-10% (9:1 MeOH/NH3) in dichloromethane to give the title compound as a yellow gum (110 mg, 12%). δH (CD3OD) 1.1 (6H, t), 1.85 (2H, m), 3.35-3.7 (6H, m), 3.9 (3H, s), 4.6(1H, t), 6.05(1H, s), 7.0(1H, t), 7.35 (1H, t), 7.45 (1H, d), 7.8 (1H, d); MS (ES+) 305 (63%, MH+). 259 (28), 213 (42), 187 (100).

Aufarbeitung

  1. customVolatile material was removed in vacuo
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe ethyl acetate soluble material was purified by chromatography on silica gel eluting with 0-10% (9:1 MeOH/NH3) in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-fcb17d0f57c94b68a1f51147d729c3f6
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06320051B1

Verknüpfte Notizen

Wird geladen…