Water → 4-[n-(4-Hydroxybenzyl)-n-(4-methoxyphenyl)amino]benzonitrile

HRID 1883679Notes

Reaction equation

HRID 1883679 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[BH4-].[Na+].[Si]([O:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Cl)=[CH:30][CH:29]=1)(C(C)(C)C)(C)C.O>CN(C)C=O>[OH:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][N:9]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 113335704-((4-Methoxyphenyl)amino)benzonitrileHCID 113688854-(Tert-butyldimethylsilyloxy)benzyl chloride

Product 1

HCID 235085154-[n-(4-Hydroxybenzyl)-n-(4-methoxyphenyl)amino]benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

224 mg of 4-[N(4-methoxyphenyl)amino]benzonitrile was dissolved in 1.2 ml of N,N-dimethylformamide, and 48 mg of sodium borohydride was added thereto under cooling with ice, followed by stirring at room temperature for 30 minutes. The previously prepared 4-(t-butyldimethylsilyloxy)benzyl chloride was dissolved in 1.2 ml of N,N- dimethylformamide and added to the reaction mixture under cooling with ice, followed by stirring at room temperature for 2 days. After water was added to the reaction mixture, the product was extracted with ethyl acetate. After the extract was washed with water and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was dissolved in 1.2 ml of tetrahydrofuran, and 1.2 ml of a 1 M tetrahydrofuran solution of tetrabutylammonium fluoride was added thereto, followed by stirring at room temperature for 15 minutes. After a saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, the product was extracted with ethyl acetate. After the extract was washed with water and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (using ethyl acetate as the eluent) to obtain 229 mg of 4-[N-(4-hydroxybenzyl)-N-(4-methoxyphenyl)amino]benzonitrile.

Workup

  1. temperatureunder cooling with ice
  2. additionadded to the reaction mixture
  3. temperatureunder cooling with ice
  4. stirringby stirring at room temperature for 2 days
  5. extractionthe product was extracted with ethyl acetate
  6. washAfter the extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. dissolutionThe resulting residue was dissolved in 1.2 ml of tetrahydrofuran
  10. addition1.2 ml of a 1 M tetrahydrofuran solution of tetrabutylammonium fluoride was added
  11. stirringby stirring at room temperature for 15 minutes
  12. additionAfter a saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture
  13. extractionthe product was extracted with ethyl acetate
  14. washAfter the extract was washed with water
  15. dry with materialdried over anhydrous sodium sulfate
  16. distillationthe solvent was distilled off under reduced pressure
  17. customThe resulting crude product was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-458b36073fc7474abd523ee386cf498d
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

Loading…