Water → 4-Benzyloxyaniline

HRID 1762873Notes

Reaction equation

HRID 1762873 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].O>C(Cl)(Cl)Cl.CO>[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([NH2:14])=[CH:15][CH:16]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 27238314-Benzyloxyaniline hydrochloride

Product 1

HCID 228604-Benzyloxyaniline

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

A 20 g portion of 4-benzyloxyaniline hydrochloride was dissolved in chloroform-methanol and made basic with a solution of 70 mL of 1.25N sodium hydroxide and 70 mL of water. The layers were separated, the aqueous phase extracted with chloroform, the chloroform extracts washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was evaporated to yield 17 g of 4-benzyloxyaniline. A solution of 2 g (0.01 mol) of 4-benzyloxyaniline, 2.26 ml (0.015 mol) of 7-bromoheptanenitrile and 7.6 g (0.05 mol) of cesium fluoride in 20 mL of DMF was stirred and heated at 100° C. for two hours. The reaction was cooled and poured into saturated sodium chloride solution and extracted with ether. The ether extracts were washed three times with saturated sodium chloride solution, dried over magnesium sulfate and concentrated to 2.9 g of oil. The oil was chromatographed on 100 g of silica gel using a gradient from 10-30% ethyl acetate in hexane. There was obtained 2.55 g (85%) of 7-[(4-benzyloxyphenyl)amino]heptanenitrile. The benzyloxy compound was treated with eight parts of 48% HBr at room temperature for 5 hours to yield impure 7-[(4-hydroxyphenyl)amino]heptanenitrile.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase extracted with chloroform
  3. washthe chloroform extracts washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-747c190ea33247c8aff763b13bcb9538
Source dataset
uspto-grants-1989_05
Patent number
US04835180

Reaction notes

Loading…