Potassium Hydroxide → N-(3-Hydroxycarbonylphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea

HRID 1857294Notes

Reaction equation

HRID 1857294 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]([NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[C:32]4[C:27](=[CH:28][C:29]([O:35][CH3:36])=[C:30]([O:33][CH3:34])[CH:31]=4)[N:26]=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)=[O:14])[CH:9]=[CH:10][CH:11]=1)=[O:5])C.[OH-].[K+]>CO>[OH:5][C:4]([C:6]1[CH:7]=[C:8]([NH:12][C:13]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][C:23]3[C:32]4[C:27](=[CH:28][C:29]([O:35][CH3:36])=[C:30]([O:33][CH3:34])[CH:31]=4)[N:26]=[CH:25][CH:24]=3)=[CH:20][CH:21]=2)=[O:14])[CH:9]=[CH:10][CH:11]=1)=[O:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22132740HCID 22132740, compound

Product 1

HCID 22132779N-(3-Hydroxycarbonylphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}ureaYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(3-Ethoxycarbonylphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea (190 mg) obtained in Example 197 was dissolved in methanol (3 ml), 35% aqueous potassium hydroxide (5 ml) was added, and the admixture was stirred at room temperature for 30 minutes. After removing methanol by reduced-pressure distillation and neutralizing using dilute hydrochloric acid, the separated crystals were filtered to obtain 67 mg of the title compound (yield: 38%).

Workup

  1. customAfter removing methanol
  2. distillationby reduced-pressure distillation
  3. filtrationthe separated crystals were filtered

Sources & evidence

ORD record
ord-42322b833d6d46d4889d6c830cd7dea5
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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