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

HRID 430062Notes

Reaction equation

HRID 430062 reaction equation
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

Participants

4

Reactant 2

HCID 1045PutrescineHCID 123691662-Chloro-4-methoxyquinoline

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-918e11715e534a4cb6a78f499bb40b68
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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