2-Amino-5-chloropyridine → HCID 22667217, compound

HRID 1008368Notes

Reaction equation

HRID 1008368 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[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([CH3:23])[C:17]=1[CH3:24].Cl[C:26](Cl)([O:28]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:37][C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][N:39]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C.ClCCl>[Cl:44][C:41]1[CH:42]=[CH:43][C:38]([NH:37][C:26]([NH:20][C:19]2[CH:21]=[CH:22][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)=[C:17]([CH3:24])[C:18]=2[CH3:23])=[O:28])=[N:39][CH:40]=1

Participants

8

Reactant 4

HCID 661742-Amino-5-chloropyridineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 218904394-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline

Product 1

HCID 22667217HCID 22667217, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethyl-aniline (3.00 g) was dissolved in chloroform (150 ml) and triethylamine (6 ml), and a solution of triphosgene (2.74 g) in dichloromethane was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, 2-amino-5-chloropyridine (2.38 g) was added to the reaction solution, and the mixture was then stirred at room temperature for additional 2 hr. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by chromatography on silica gel by development with chloroform/methanol (20/1) to give 3.4 g (yield 77%) of the title compound.

Workup

  1. stirringthe mixture was then stirred at room temperature for additional 2 hr
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customthe residue was purified by chromatography on silica gel by development with chloroform/methanol (20/1)

Sources & evidence

ORD record
ord-bff5c1ab00d34b1d9626d39de44923dc
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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