Hydrochloric Acid → HCID 21889971, compound

HRID 721603Notes

Reaction equation

HRID 721603 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=O)[CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=4)[N:23]=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)=[CH:5][CH:4]=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:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21891203HCID 21891203, compound

Product 1

HCID 21889971HCID 21889971, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N1-(4-Methoxyphenyl)-2-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenoxy}acetamide (90 mg) was dissolved in tetrahydrofuran (10 ml) to prepare a solution. A borane-tetrahydrofuran complex (1.0 M solution: 0.98 ml) was then added to the solution, and the mixture was heated under reflux for 3 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 (52 mg, yield 60%).

Workup

  1. customto prepare a solution
  2. additionA borane-tetrahydrofuran complex (1.0 M solution: 0.98 ml) was then added to the solution
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 3 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-b225fac4d8dc4fea85d13426d18ac1b7
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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