Propylamine → HCID 22667083, compound

HRID 1008355Notes

Reaction equation

HRID 1008355 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].ClC(Cl)(O[C:28](=[O:34])OC(Cl)(Cl)Cl)Cl.[CH2:36](N)[CH2:37][CH3:38].C(=O)([O-])O.[Na+].C([N:47](CC)CC)C>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[N:4]([CH2:36][CH2:37][CH3:38])[C:28]([NH2:47])=[O:34]

Participants

7

Reactant 5

HCID 7852PropylamineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 112212234-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-chloroaniline

Product 1

HCID 22667083HCID 22667083, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (100 mg) was dissolved in chloroform (7.5 ml) and triethylamine (1 ml), and a solution of triphosgene (99 mg) in chloroform was then added to the solution. The mixture was heated under reflux for 5 min. Next, n-propylamine (21 mg) was added to the reaction solution, and the mixture was heated under reflux for additional 2 hr. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was supported on diatomaceous earth, followed by extraction with chloroform. The solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel by development with chloroform/methanol (8/1). Thus, the title compound was quantitatively obtained.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 min
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for additional 2 hr
  5. extractionfollowed by extraction with chloroform
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customThe residue was purified by chromatography on silica gel by development with chloroform/methanol (8/1)

Sources & evidence

ORD record
ord-8d5ceb1c6a5e4ad2a974f5bb25b6e8f0
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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