Ethylenediamine → HCID 18353720, compound

HRID 430061Notes

Reaction equation

HRID 430061 reaction equation
Cl[C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:15]([NH2:18])[CH2:16][NH2:17]>>[NH2:17][CH2:16][CH2:15][NH:18][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 8174292-Chloro-4-ethoxyquinoline

Product 1

HCID 18353720HCID 18353720, compoundYield 67%

Procedure

2-Chloro-4-ethoxyquinoline (1.119 g, 5.39 mmol) and ethylenediamine (10.8 ml, 162 mmol) were heated at 60° C. for 50 h, then evaporated to dryness. The residue was purified by flash chromotography on silica gel, eluting with 0-14% ‘10% ammonia in methanol’ in dichloromethane, to give 2-(2-aminoethylamino)-4-ethoxyquinoline (0.830 g, 67%). This material (0.820 g, 3.54 mmol) was dissolved in concentrated hydrochloric acid (25 ml) and gently refluxed for 16 h. The mixture was then cooled in an ice bath, and the precipitate filtered off and dried in vacuo to give the title compound as an off-white powder (0.861 g, 88%); δH (CD3OD) 3.2-3.35(2H, m, under methanol), 3.84 (2H, t), 6.35 (1H, s), 7.46 (1H, t), 7.7-7.9 (2H, m), 8.1 (1H, d), MS (ES+) 204 (50%, MH+) and 187 (100).

Workup

  1. customevaporated to dryness
  2. customThe residue was purified by flash chromotography on silica gel
  3. washeluting with 0-14% ‘10% ammonia in methanol’ in dichloromethane

Sources & evidence

ORD record
ord-0d26c13fdbbc4d8abd2619e6dd0d47e5
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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