Methanol → HCID 22667193, compound

HRID 1008361Notes

Reaction equation

HRID 1008361 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.[NH2:36][C:37]1[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][N:38]=1.CO>C(Cl)(Cl)Cl.C(N(CC)CC)C.ClCCl>[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[NH:4][C:28]([NH:36][C:37]1[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][N:38]=1)=[O:34]

Participants

8

Reactant 4

HCID 887MethanolHCID 153482-Amino-5-methylpyridineHCID 94429TriphosgeneHCID 112212234-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-chloroaniline

Product 1

HCID 22667193HCID 22667193, compoundYield 69.4%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

2-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (122 mg) was dissolved in chloroform (10 ml) and triethylamine (1 ml), and a solution of triphosgene (110 mg) in dichloromethane was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, 2-amino-5-picoline (120 mg) was added to the reaction solution, and the mixture was stirred at room temperature for 2 hr. Methanol was added to the reaction solution, and the solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel by development with chloroform/acetone (2/1) to give 119 mg (yield 69%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. customthe solvent was removed by distillation under the reduced pressure
  3. customThe residue was purified by chromatography on silica gel by development with chloroform/acetone (2/1)

Sources & evidence

ORD record
ord-f93ce8bca4b842ccba07fe56492f4c15
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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