Sodium Hydroxide → 4-Chloro-3-(2-dimethylamino-ethoxy)aniline

HRID 1419819Notes

Reaction equation

HRID 1419819 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[O:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15].Cl[Sn]Cl.[OH-].[Na+]>CCO.Cl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[O:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 544873904-Chloro-3-(2-dimethylaminoethoxy)nitrobenzene

Product 1

HCID 121354204-Chloro-3-(2-dimethylamino-ethoxy)anilineYield 94.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To 4-chloro-3-(2-dimethylaminoethoxy)nitrobenzene (1.5 g 0.006 mol) in EtOH (25 ml) at 60° C., was added SnCl2 (4.2 g) in concentrated hydrochloric acid (7.6 ml) dropwise. The mixture was then heated under reflux for 30 mins and after cooling to room temperature, diluted with water (50 ml), and basified by addition of 40% aq. sodium hydroxide. The mixture was extracted into CH2Cl2 and the combined organic layers, dried (Na2SO4) and concentrated in vacuo to give the title compound as a brown oil (1.22 g, 93%).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 30 mins
  3. extractionThe mixture was extracted into CH2Cl2
  4. dry with materialthe combined organic layers, dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1560b02670ae4597856ee3c8c74fac15
Source dataset
uspto-grants-1999_03
Patent number
US05889022

Reaction notes

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