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

HRID 433161Notes

Reaction equation

HRID 433161 reaction equation
Cl[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].C(N(CC)CC)C.[NH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27]>ClCCl>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27])=[CH:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 258684-Amino-1-butanolHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 121061814-[(3-Nitroquinolin-4-yl)amino]butan-1-olYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round bottom flask was charged with a magnetic stir bar, 4-chloro-3-nitroquinoline (109.70 g, 525.87 mmol) and dichloromethane (500 mL). To the solution was added triethylamine (79.82 g, 788.81 mmol) and 4-amino-1-butanol (46.87 g, 525.87 mmol) to give a homogeneous, dark yellow solution. The reaction was judged to be complete after heating at reflux for 30 minutes. The solution was cooled and then partitioned between chloroform and saturated aqueous ammonium chloride. The layers were separated and the aqueous layer was extracted with chloroform (1×). The organic layers were combined and then concentrated under reduced pressure to afford 4-[(3-nitroquinolin-4-yl)amino]butan-1-ol (104.67 g, 400.60 mmol) as a dark yellow solid. This material was used without further purification.

Workup

  1. additionA round bottom flask was charged with a magnetic stir bar
  2. customto give a homogeneous, dark yellow solution
  3. temperatureafter heating
  4. temperatureat reflux for 30 minutes
  5. temperatureThe solution was cooled
  6. custompartitioned between chloroform and saturated aqueous ammonium chloride
  7. customThe layers were separated
  8. extractionthe aqueous layer was extracted with chloroform (1×)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ff0550895e064b2bbf4920f14780ad4f
Source dataset
uspto-grants-2003_12
Patent number
US06667312B2

Reaction notes

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