Thionyl Chloride → HCID 22320532, compound

HRID 897193Notes

Reaction equation

HRID 897193 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]O)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].S(Cl)([Cl:21])=O>ClCCl>[Cl:21][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

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13958331HCID 13958331, compound

Product 1

HCID 22320532HCID 22320532, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round bottom flask was charged with a magnetic stir bar, 3-[(3-nitroquinolin-4-yl)amino]propan-1-ol (20.75 g, 83.93 mmol), thionyl chloride (15.0 g, 125.89 mmol), and dichloromethane (420 mL). The bright yellow, homogeneous solution was stirred at ambient temperature for 2 hours at which time the starting material was completely consumed. The volatiles were removed under reduced pressure and the resulting solid stirred in water (400 mL) made basic (pH 10) with solid sodium carbonate. A bright yellow solid was collected by filtration to afford N-(3-chloropropyl)-3-nitroquinolin-4-amine (21.63 g, 81.41 mmol) which was used without further purification.

Workup

  1. additionA round bottom flask was charged with a magnetic stir bar
  2. customwas completely consumed
  3. customThe volatiles were removed under reduced pressure
  4. stirringthe resulting solid stirred in water (400 mL)
  5. filtrationA bright yellow solid was collected by filtration

Sources & evidence

ORD record
ord-4dbb1173036146feb92f96f4853ec401
Source dataset
uspto-grants-2005_07
Patent number
US06921826B2

Reaction notes

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