Putrescine → 2-(4-Aminobut-1-ylamino)-4-methoxyquinoline

HRID 430062

Reaktionsgleichung

Reaktionsgleichung von HRID 430062
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][CH2:17][CH2:18][NH2:19]>ClCCl>[NH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][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

Komponenten

4

Edukt 2

HCID 1045PutrescineHCID 123691662-Chloro-4-methoxyquinoline

Produkt 1

HCID 183537062-(4-Aminobut-1-ylamino)-4-methoxyquinolineAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Chloro-4-methoxyquinoline (prepared as for 2-chloro-4-ethoxyquinoline but using methanol as solvent; 3.873 g, 20 mmol) and 1,4-diaminobutane (12.3 g, 140 mmol) were heated at 60° C. for 50 h. The solution was then reduced in volume in vacuo, and diluted with dichloromethane. The solid was filtered off and washed with dichloromethane. The filtrate was evaporated to dryness and purified by flash chromatography, eluting with 0-10% ‘10% ammonia in methanol’ in dichloromethane, to give 2-(4-aminobut-1-ylamino)-4-methoxyquinoline as a white solid (2.29 g, 47%). This material (2.142 g, 8.73 mmol) in concentrated hydrochloric acid (80 ml) was gently refluxed for 15 h, and then evaporated to dryness to give the title compound as a white foam (2.65 g, 99%); δH (CD3OD) 1.8-1.9 (4H, m), 2.95-3.05 (2H, m), 3.5-3.6 (2H, m), 6.36 (1H, s), 7.46 (1H, t), 7.7-7.9 (2H, m), 8.45(1H, d): MS (ES+) 232 (100%, MH+).

Aufarbeitung

  1. filtrationThe solid was filtered off
  2. washwashed with dichloromethane
  3. customThe filtrate was evaporated to dryness
  4. custompurified by flash chromatography
  5. washeluting with 0-10% ‘10% ammonia in methanol’ in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-918e11715e534a4cb6a78f499bb40b68
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06320051B1

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