4-Chloro-3-(2-dimethylaminoethoxy)nitrobenzene → 4-Chloro-3-(2-dimethylamino-ethoxy)aniline

HRID 2392650Notes

Reaction equation

HRID 2392650 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([N+:13]([O-])=O)[CH:9]=[CH:10][C:11]=1[Cl:12]>C(O)C.Cl.O.[OH-].[Na+]>[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][C:11]=1[Cl:12])[NH2:13]

Participants

6

Reactant 1

HCID 544873904-Chloro-3-(2-dimethylaminoethoxy)nitrobenzene

Product 1

HCID 121354204-Chloro-3-(2-dimethylamino-ethoxy)aniline

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-(2dimethylaminoethoxy)-4chloronitrobenzene (D57) (295 mg) in ethanol (5 ml) was heated to 60° C. and treated dropwise with a solution of stannous chloride (0.82 g) in concentrated hydrochloric acid (1.5 ml) with stiring. After heating to reflux for 1/2 h, the reaction mixture was cooled, diluted with water and basified with 40% NaOH, then extracted into dichloromethane. The dried (Na2SO4) organic phase was evaporated under reduced pressure to give the title compound as a yellow oil. (221 mg, 85%).

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 1/2 h
  3. temperaturethe reaction mixture was cooled
  4. extractionextracted into dichloromethane
  5. dry with materialThe dried (Na2SO4) organic phase
  6. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-34a104fe78194449981b38d5136e2c98
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

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