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

HRID 399263Notes

Reaction equation

HRID 399263 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)aniline

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To 4-chloro-3-(2-dimethylaminoethoxy)nitrobenzene (D5, 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.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 30 mins

Sources & evidence

ORD record
ord-6d7b108b4a9b4fe387f0badb00bf8f8d
Source dataset
uspto-grants-1998_10
Patent number
US05817833

Reaction notes

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