Hydrochloric Acid → HCID 21890044, compound

HRID 721599Notes

Reaction equation

HRID 721599 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=O)[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[C:29]3[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=3)[N:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1.Cl.[OH-].[Na+]>O1CCCC1>[CH3:31][O:30][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][C:26]=1[O:32][CH3:33])[N:23]=[CH:22][CH:21]=[C:20]2[O:19][C:16]1[CH:15]=[CH:14][C:13]([O:12][CH2:11][CH2:10][NH:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21891184HCID 21891184, compound

Product 1

HCID 21890044HCID 21890044, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N1-(2-Methoxyphenyl)-2-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenoxy}acetamide (100 mg) was dissolved in tetrahydrofuran (10 ml) to prepare a solution. A borane-tetrahydrofuran complex (1.0 M solution: 1.08 ml) was then added to the solution, and the mixture was heated under reflux for 5 hr. 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 (58 mg, yield 60%).

Workup

  1. customto prepare a solution
  2. additionA borane-tetrahydrofuran complex (1.0 M solution: 1.08 ml) was then added to the solution
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 5 hr
  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-fd6ef86711a840a1bf476a148c1b2dc5
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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