Methanol → HCID 69351572, compound

HRID 1375798Notes

Reaction equation

HRID 1375798 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].ClC(Cl)(O[C:29](=[O:35])OC(Cl)(Cl)Cl)Cl.[NH2:37][C:38]1[N:43]=[C:42]([CH3:44])[CH:41]=[CH:40][CH:39]=1.CO>C(Cl)(Cl)Cl.C(N(CC)CC)C.ClCCl>[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]([NH:20][C:29]([NH:37][C:38]2[CH:39]=[CH:40][CH:41]=[C:42]([CH3:44])[N:43]=2)=[O:35])=[C:18]([CH3:23])[C:17]=1[CH3:24]

Participants

8

Reactant 4

HCID 887MethanolHCID 157652-Amino-6-methylpyridineHCID 94429TriphosgeneHCID 218904394-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline

Product 1

HCID 69351572HCID 69351572, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline (120 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 heated under reflux overnight. 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 (40/60) to give 64 mg (yield 38%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. customthe solvent was removed by distillation under the reduced pressure
  4. customThe residue was purified by chromatography on silica gel by development with chloroform/acetone (40/60)

Sources & evidence

ORD record
ord-e3dc5ad7a8044178a9fd332f3785884a
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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