Methanol → HCID 22667209, compound

HRID 1375796Notes

Reaction equation

HRID 1375796 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[N:42]=[C:41]([CH3:43])[CH:40]=[CH:39][CH: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:38]=[CH:39][CH:40]=[C:41]([CH3:43])[N:42]=1)=[O:34]

Participants

8

Reactant 4

HCID 887MethanolHCID 157652-Amino-6-methylpyridineHCID 94429TriphosgeneHCID 112212234-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-chloroaniline

Product 1

HCID 22667209HCID 22667209, compoundYield 42.6%

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, 6-amino-2-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 73 mg (yield 42%) 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-7c73a17618a346e7a13d08baa0b7935e
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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