Thionyl Chloride → HCID 22320532, compound

HRID 432850Notes

Reaction equation

HRID 432850 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-b8e815051f4e4674a0aeb396c211975b
Source dataset
uspto-grants-2003_12
Patent number
US06664264B2

Reaction notes

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