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

HRID 430062

反応式

HRID 430062 の反応式
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

参加物

4

反応物 2

HCID 1045PutrescineHCID 123691662-Chloro-4-methoxyquinoline

生成物 1

HCID 183537062-(4-Aminobut-1-ylamino)-4-methoxyquinoline収率 47%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-918e11715e534a4cb6a78f499bb40b68
出典データセット
uspto-grants-2001_11
特許番号
US06320051B1

関連ノート

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