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

HRID 430062

반응식

HRID 430062 반응식
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

참가 물질

4

반응물 2

HCID 1045PutrescineHCID 123691662-Chloro-4-methoxyquinoline

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-918e11715e534a4cb6a78f499bb40b68
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06320051B1

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