Hydrochloric Acid → HCID 21890595, compound

HRID 721607Notes

Reaction equation

HRID 721607 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=O)[CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[C:28]4[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=4)[N:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.Cl.[OH-].[Na+]>O1CCCC1>[CH3:30][O:29][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][C:25]=1[O:31][CH3:32])[N:22]=[CH:21][CH:20]=[C:19]2[O:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21890886HCID 21890886, compound

Product 1

HCID 21890595HCID 21890595, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N1-(3-Methylphenyl)-2-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenoxy}acetamide (70 mg) was dissolved in tetrahydrofuran (10 ml) to prepare a solution. A borane-tetrahydrofuran complex (1.0 M solution: 0.78 ml) was then added to the solution, and the mixture was heated under reflux overnight. 1 N Hydrochloric acid was added thereto, and the mixture was further heated under reflux for 30 min. A 5% aqueous sodium hydroxide solution was added to the reaction solution, the mixture was extracted with chloroform, and the extract was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin-layer chromatography using chloroform/methanol for development to give the title compound (31 mg, yield 46%).

Workup

  1. customto prepare a solution
  2. additionA borane-tetrahydrofuran complex (1.0 M solution: 0.78 ml) was then added to the solution
  3. temperaturethe mixture was heated
  4. temperatureunder reflux overnight
  5. temperaturethe mixture was further heated
  6. temperatureunder reflux for 30 min
  7. extractionthe mixture was extracted with chloroform
  8. dry with materialthe extract was dried over anhydrous sodium sulfate
  9. customThe solvent was removed by distillation under the reduced pressure
  10. customThe residue was purified by thin-layer chromatography

Sources & evidence

ORD record
ord-f4f43e98914042689aeded1f0c0b5d4c
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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