Ethanolamine → 2-[(3-Nitro-4-quinolinyl)amino]ethanol

HRID 987188Notes

Reaction equation

HRID 987188 reaction equation
S(Cl)(Cl)=O.CN(C)C=O.O[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22].C(N(CC)CC)C.[CH2:31]([CH2:33][NH2:34])[OH:32]>ClCCl>[N+:21]([C:12]1[CH:13]=[N:14][C:15]2[C:20]([C:11]=1[NH:34][CH2:33][CH2:31][OH:32])=[CH:19][CH:18]=[CH:17][CH:16]=2)([O-:23])=[O:22]

Participants

7

Reactant 5

HCID 700Ethanolamine2×HCID 6228DimethylformamideHCID 8471Triethylamine2×HCID 24386Thionyl ChlorideHCID 178526762HCID 178526762, compound

Product 1

HCID 130073542-[(3-Nitro-4-quinolinyl)amino]ethanolYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (32.3 mL, 0.4338 mole) and N,N-dimethylformamide (32 mL, 0.4338 mole) were added sequentially to a suspension of 4-hydroxy-3-nitroquinoline (75 g, 0.3944 mole) in dichloromethane (750 ml). The reaction mixture was heated at reflux for about 2½ hours and then held at ambient temperature overnight. The reaction mixture was chilled in an ice bath and then a mixture of triethylamine (82.5 mL, 0.5916 moles) and ethanolamine (35.7 mL, 0.5916 mole) in dichloromethane was slowly added. The reaction mixture was heated at reflux for several hours and then an additional 0.5 equivalents of both triethylamine and ethanolamine were added. The reaction mixture was refluxed for an additional hour then held at ambient temperature overnight. The resulting solid was isolated by filtration, washed first with dichloromethane then with water, and dried to provide 75 g of 2-[(3-nitro-4-quinolinyl)amino]ethanol.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for about 2½ hours
  3. temperatureThe reaction mixture was chilled in an ice bath
  4. additionwas slowly added
  5. temperatureThe reaction mixture was heated
  6. temperatureat reflux for several hours
  7. temperatureThe reaction mixture was refluxed for an additional hour
  8. waitthen held at ambient temperature overnight
  9. customThe resulting solid was isolated by filtration
  10. washwashed first with dichloromethane
  11. dry with materialwith water, and dried

Sources & evidence

ORD record
ord-7123f9cf396b4ff2a6100c9efb869ef3
Source dataset
uspto-grants-2003_10
Patent number
US06630588B2

Reaction notes

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