Dichloromethane → HCID 22320532, compound

HRID 1182236Notes

Reaction equation

HRID 1182236 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.C(=O)([O-])[O-].[Na+].[Na+]>O>[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

6

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 13958331HCID 13958331, compound

Product 1

HCID 22320532HCID 22320532, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 he 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 and he
  4. customresulting solid
  5. filtrationA bright yellow solid was collected by filtration

Sources & evidence

ORD record
ord-c91002227b26411aa9412a32e5724fe1
Source dataset
uspto-grants-2007_10
Patent number
US07288550B2

Reaction notes

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