Hydrochloric Acid → HCID 21890319, compound

HRID 721673Notes

Reaction equation

HRID 721673 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[C:21]([CH3:22])=[CH:20][C:19]([NH:23][C:24](=O)[CH2:25][CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])=[C:18]([CH3:36])[CH:17]=1.Cl.[OH-].[Na+]>O1CCCC1>[Cl:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[O:27][CH2:26][CH2:25][CH2:24][NH:23][C:19]1[CH:20]=[C:21]([CH3:22])[C:16]([O:15][C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][CH:7]=2)=[CH:17][C:18]=1[CH3:36]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21890980HCID 21890980, compound

Product 1

HCID 21890319HCID 21890319, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

N1-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,5-dimethylphenyl}-3-(2-chlorophenoxy)propaneamide (200 mg) was dissolved in tetrahydrofuran (10 ml) to prepare a solution. A 1 M solution (1.3 ml) of a borane-tetrahydrofuran complex in tetrahydrofuran was then added to the solution, and the mixture was stirred with heating under reflux for 2 hr. The reaction solution was cooled to 0° C. and was adjusted to pH=1 by the addition of 1 N hydrochloric acid, followed by stirring with heating under reflux for 30 min. The reaction solution was cooled to 0° C., was adjusted to pH=12 by the addition of a 1 N aqueous sodium hydroxide solution, and was extracted with chloroform. After the concentration of the extract, the residue was purified on a column using chloroform/methanol to give the title compound (156 mg, yield 80%). Mass spectrometry value (ESI-MS, m/z): 494 (M++1)

Workup

  1. customto prepare a solution
  2. temperaturewith heating
  3. temperatureunder reflux for 2 hr
  4. stirringby stirring
  5. temperaturewith heating
  6. temperatureunder reflux for 30 min
  7. temperatureThe reaction solution was cooled to 0° C.
  8. extractionwas extracted with chloroform
  9. customAfter the concentration of the extract, the residue was purified on a column

Sources & evidence

ORD record
ord-f6eb79419edb4e37bf43e7ba603e7a97
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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