Phosphorus oxychloride → 4-Chloro-3-nitroquinoline

HRID 1187429Notes

Reaction equation

HRID 1187429 reaction equation
P(Cl)(Cl)([Cl:3])=O.[N+:6]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1O)=[CH:16][CH:15]=[CH:14][CH:13]=2)([O-:8])=[O:7]>CN(C=O)C>[Cl:3][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][C:9]=1[N+:6]([O-:8])=[O:7]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526762HCID 178526762, compound

Product 1

HCID 112758084-Chloro-3-nitroquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphorous oxychloride (84.3 g, 0.55 mol) was added to a stirred suspension of 3-nitroquinolin-4-ol (95.0 g, 0.50 mol) in DMF (500 mL), and an exotherm was observed. After the addition was complete, the solution was heated on a steam bath for 15 minutes. The solution was poured over ice to precipitate 4-chloro-3-nitroquinoline. The 4-chloro-3-nitroquinoline was isolated by filtration, washed with water, and pressed dry. The 4-chloro-3-nitroquinoline was dissolved in dichloromethane (1 L) and the solution was dried over magnesium sulfate and filtered. 2-(2-Aminoethoxy)ethanol (60.7 g, 0.6 mol) and triethylamine (104 mL, 0.75 mol) were added to the filtrate. The resulting solution was heated at reflux for 30 minutes. The mixture was concentrated under reduced pressure. The residue was dissolved in dilute aqueous hydrochloric acid and filtered. Ammonium hydroxide was added to the filtrate and a yellow solid formed. The solid was isolated by filtration, washed with water, and dried to provide 104.5 g of 2-{2-[(3-nitroquinolin-4-yl)aniino]ethoxy}ethanol as a yellow solid.

Workup

  1. additionAfter the addition
  2. temperaturethe solution was heated on a steam bath for 15 minutes
  3. additionThe solution was poured over ice
  4. customto precipitate 4-chloro-3-nitroquinoline

Sources & evidence

ORD record
ord-7ee774d4e54246e2b248c1e4310c319a
Source dataset
uspto-grants-2014_03
Patent number
US08673932B2

Reaction notes

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