4-Chloro-2-toluidine → HCID 22667178, compound

HRID 1375801Notes

Reaction equation

HRID 1375801 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:22]([CH3:23])=[CH:21][C:19]([NH2:20])=[C:18]([CH3:24])[CH:17]=1.Cl[C:26](Cl)([O:28]C(=O)OC(Cl)(Cl)Cl)Cl.[Cl:37][C:38]1[CH:44]=[CH:43][C:41]([NH2:42])=[C:40]([CH3:45])[CH:39]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C.ClCCl>[Cl:37][C:38]1[CH:44]=[CH:43][C:41]([NH:42][C:26]([NH:20][C:19]2[CH:21]=[C:22]([CH3:23])[C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:17][C:18]=2[CH3:24])=[O:28])=[C:40]([CH3:45])[CH:39]=1

Participants

8

Reactant 4

HCID 72514-Chloro-2-toluidineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 218904214-((6,7-Dimethoxyquinolin-4-yl)oxy)-2,5-dimethylaniline

Product 1

HCID 22667178HCID 22667178, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,5-dimethylaniline (100 mg) was dissolved in chloroform (10 ml) and triethylamine (1 ml), and a solution of triphosgene (92 mg) in dichloromethane was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, 4-chloro-2-methylaniline (44 μl) was added to the reaction solution, and the mixture was stirred at room temperature overnight. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, followed by extraction with chloroform. The chloroform layer was dried over sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was dissolved in a minor amount of chloroform, and a large amount of ether was added to the solution to precipitate a crystal which was then collected by filtration to give 118 mg (yield 78%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe chloroform layer was dried over sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. dissolutionThe residue was dissolved in a minor amount of chloroform
  6. additiona large amount of ether was added to the solution
  7. customto precipitate a crystal which
  8. filtrationwas then collected by filtration

Sources & evidence

ORD record
ord-08f83370ef894b41accd572efb9d2c4f
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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