Thionyl Chloride → HCID 22320534, compound

HRID 433172Notes

Reaction equation

HRID 433172 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]O)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].S(Cl)([Cl:23])=O>>[Cl:23][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 22320448HCID 22320448, compound

Product 1

HCID 22320534HCID 22320534, compoundYield 4,805.9%

Conditions

Temperature
80 °C

Procedure

A round bottom flask was charged with a magnetic stir bar, 5-[(3-nitroquinolin-4-yl)amino]pentan-1-ol (5.0 g, 18.16 mmol), and thionyl chloride (40.78 g, 0.34 mmol) under a nitrogen atmosphere. The reaction mixture was heated to 80° C. to give a homogeneous solution that was maintained at 80° C. for 1 hour at which time the starting material was completely consumed. The volatiles were removed under reduced pressure and the resulting oil stirred in water made basic (pH 10) with solid sodium carbonate. The resulting solid was collected by filtration to afford N-(5-chloropentyl)-3-nitroquinolin-4-amine (4.80 g, 16.34 mmol) which was used without further purification.

Workup

  1. additionA round bottom flask was charged with a magnetic stir bar
  2. customto give a homogeneous solution that
  3. temperaturewas maintained at 80° C. for 1 hour at which time the starting material
  4. customwas completely consumed
  5. customThe volatiles were removed under reduced pressure
  6. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-a62d2c3cb1e04390b74730cf622fab6a
Source dataset
uspto-grants-2003_12
Patent number
US06667312B2

Reaction notes

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