Ethanol → Benzenamine, 5-(2,4-dichlorophenoxy)-2-nitro-

HRID 463603Notes

Reaction equation

HRID 463603 reaction equation
CC([NH:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])[CH:8]=[CH:7][C:6]=1[N+:20]([O-:22])=[O:21])=O.C(O)C.[OH-].[Na+]>Cl>[N+:20]([C:6]1[CH:7]=[CH:8][C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])=[CH:10][C:5]=1[NH2:4])([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 20261995HCID 20261995, compound

Product 1

HCID 134464Benzenamine, 5-(2,4-dichlorophenoxy)-2-nitro-

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

N-methylcarbonyl 2-nitro-5-(2,4-dichlorophenoxy)aniline (2.0 g, 5.9 mmol) in 50 ml of 10% hydrochloric acid is heated under reflux for 2 hours. The reaction is cooled to RT, 10 ml of ethanol is added, and the reaction is heated under reflux for another 4 hours. The reaction is cooled to RT, made slightly basic with 20% sodium hydroxide and extracted with ether. The combined extracts are washed with water, dried and stripped to give 2-nitro-5-(2,4-dichlorophenoxy)aniline.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperaturethe reaction is heated
  3. temperatureunder reflux for another 4 hours
  4. temperatureThe reaction is cooled to RT
  5. extractionextracted with ether
  6. washThe combined extracts are washed with water
  7. customdried

Sources & evidence

ORD record
ord-924deeea753240c294441409db0367ac
Source dataset
uspto-grants-1985_10
Patent number
US04544400

Reaction notes

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