Methanol → HCID 22667114, compound

HRID 1008372Notes

Reaction equation

HRID 1008372 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[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][N: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:43]=[CH:42][C:41]([CH3:44])=[CH:40][N:39]=2)=[O:35])=[C:18]([CH3:23])[C:17]=1[CH3:24]

Participants

8

Reactant 4

HCID 887MethanolHCID 153482-Amino-5-methylpyridineHCID 94429TriphosgeneHCID 218904394-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline

Product 1

HCID 22667114HCID 22667114, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethyl-aniline (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, 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/methanol (91/9) to give 122 mg (yield 72%) 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/methanol (91/9)

Sources & evidence

ORD record
ord-18de378b9d9545f2a138f6abb9e4b13d
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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