Thionyl Chloride → HCID 22320538, compound

HRID 433195Notes

Reaction equation

HRID 433195 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][C:14]=1[N+:23]([O-:25])=[O:24]>ClCCl>[Cl:3][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][C:14]=1[N+:23]([O-:25])=[O:24]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22320550HCID 22320550, compound

Product 1

HCID 22320538HCID 22320538, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of thionyl chloride (6.74 g, 56.6 mmol) in dichloromethane (50 mL) was slowly added to a solution of N-(6-hydroxyhexyl)-3-nitroquinolin-4-amine (14.9 g, 51.5 mmol) in dichloromethane (200 mL). After the addition was complete the reaction mixture was stirred for about an hour and then it was concentrated under reduced pressure. The residue was suspended in water, slurried for about an hour, isolated by filtration, washed with water and then dried to provide 14.0 g of N-(6-chlorohexyl)-3-nitroquinolin-4-amine as a solid.

Workup

  1. additionAfter the addition
  2. concentrationit was concentrated under reduced pressure
  3. waitslurried for about an hour
  4. customisolated by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-37a19349bad545b7ba150a3775b42d3b
Source dataset
uspto-grants-2003_12
Patent number
US06667312B2

Reaction notes

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