Thionyl Chloride → 6-benzyloxy-N-(5-chloropentyl)-3-nitroquinolin-4-amine

HRID 2383143Notes

Reaction equation

HRID 2383143 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][C:17]([N+:23]([O-:25])=[O:24])=[C:16]2[NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>ClCCl>[CH2:5]([O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][C:17]([N+:23]([O-:25])=[O:24])=[C:16]2[NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][Cl:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 670509595-{[6-(Benzyloxy)-3-nitroquinolin-4-yl]amino}pentan-1-ol

Product 1

HCID 670510456-benzyloxy-N-(5-chloropentyl)-3-nitroquinolin-4-amineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, thionyl chloride (1.7 mL, 23 mmol) was added to a mixture of 5-{[6-(benzyloxy)-3-nitroquinolin-4-yl]amino}pentan-1-ol (5.95 g, 15.6 mmol) and anhydrous dichloromethane (78 mL). The reaction became homogeneous and was heated at reflux for 1.5 hours, at which time a yellow precipitate formed. The volatiles were removed under reduced pressure, and the residue was partitioned between dilute aqueous sodium carbonate (100 mL) and dichloromethane (150 mL). The aqueous layer was washed with dichloromethane (50 mL), and the combined organic solutions were washed with brine (50 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 6.24 g of 6-benzyloxy-N-(5-chloropentyl)-3-nitroquinolin-4-amine as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours, at which time a yellow precipitate
  3. customformed
  4. customThe volatiles were removed under reduced pressure
  5. customthe residue was partitioned between dilute aqueous sodium carbonate (100 mL) and dichloromethane (150 mL)
  6. washThe aqueous layer was washed with dichloromethane (50 mL)
  7. washthe combined organic solutions were washed with brine (50 mL)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aa5f72eb8090470dae38a0138c757250
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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