Water → HCID 15408653, compound

HRID 582220Notes

Reaction equation

HRID 582220 reaction equation
B.[Na].FC(F)(F)C(O)=O.CO[N:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)[CH:15]=1.O>O1CCCC1.Cl>[N+:28]([C:25]1[CH:26]=[CH:27][C:22]([CH2:21][O:20][C:16]2[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=2)[CH2:13][NH2:12])=[CH:23][CH:24]=1)([O-:30])=[O:29]

Participants

7

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 86199529HCID 86199529, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 15408653HCID 15408653, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Suspended in 160 ml of anhydrous tetrahydrofuran were 3.783 g (0.100 mol) of sodium boron hydride, and a solution of 11.402 g (0.100 mol) of trifluoroacetic acid in 20 ml of anhydrous tetrahydrofuran was added dropwise to the suspension at room temperature. The resultant mixture was stirred for 10 minutes. A solution of 5.726 g (0.02 mol) of O-methyl-3-(4-nitrobenzyloxy)benzaldoxime in 20 ml of anhydrous tetrahydrofuran was added dropwise to this mixture. The mixture was stirred at room temperature for 3 hours and heated under reflux further for 2 hours. After cooling the mixture, 20 ml of water were added under chilling with ice water, and the solvent was then distilled off under reduced pressure. The residue was extracted with chloroform, and the solvent was distilled out of the resultant extract under reduced pressure, thereby obtaining a crude product. The crude product was dissolved in 800 ml of 2 N hydrochloric acid, and the solution was washed with chloroform and then neutralized with 50% sodium hydroxide, followed by extraction with chloroform. The solvent was distilled out of the resultant extract under reduced pressure, thereby obtaining 4.234 g (yield: 82%) of the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux further for 2 hours
  3. additionwere added
  4. distillationthe solvent was then distilled off under reduced pressure
  5. extractionThe residue was extracted with chloroform
  6. distillationthe solvent was distilled out of the resultant
  7. extractionextract under reduced pressure
  8. customobtaining a crude product
  9. washthe solution was washed with chloroform
  10. extractionfollowed by extraction with chloroform
  11. distillationThe solvent was distilled out of the resultant
  12. extractionextract under reduced pressure

Sources & evidence

ORD record
ord-7e5427cbe8dd4a4c9c5a4d33a20f5cc9
Source dataset
uspto-grants-1999_07
Patent number
US05922767

Reaction notes

Loading…