Triethylamine → 4-[(3-Nitroquinolin-4-yl)amino]butan-1-ol

HRID 468565Notes

Reaction equation

HRID 468565 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].O=P(Cl)(Cl)Cl.[NH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25].C(N(CC)CC)C>CN(C=O)C.CCO>[OH:25][CH2:24][CH2:23][CH2:22][CH2:21][NH:20][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 258684-Amino-1-butanolHCID 178526762HCID 178526762, compound

Product 1

HCID 121061814-[(3-Nitroquinolin-4-yl)amino]butan-1-olYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 4-hydroxy-3-nitroquinoline (Gerster et al. J Med Chem 2005, 48, 3481) in DMF (0.7 M) was treated dropwise with POCl3 (1.2 eq) and stirred at 50° C. for 30 min. The reaction mixture was poured into ice-water and extracted twice with CH2Cl2. The combined organic layers were washed with water, dried (Na2SO4) and concentrated. The crude product obtained was added to a solution of 4-amino-butanol (1.3 eq) and triethylamine (1.9 eq) in EtOH and heated to reflux for 15 min. After concentration, flash chromatography on silica gel (gradient elution, 2→4% MeOH—CHCl3) afforded 4-(4-hydroxybutyl)amino-3-nitroquinoline as a yellow solid in 97% yield.

Workup

  1. extractionextracted twice with CH2Cl2
  2. washThe combined organic layers were washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product obtained
  6. temperatureheated
  7. temperatureto reflux for 15 min
  8. concentrationAfter concentration, flash chromatography on silica gel (gradient elution, 2→4% MeOH—CHCl3)

Sources & evidence

ORD record
ord-0402b9079c8e433382838b1ff0194a7b
Source dataset
uspto-grants-2014_01
Patent number
US08624029B2

Reaction notes

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