Hydrochloric Acid → 2-Nitro-4-phenoxyaniline

HRID 2089559Notes

Reaction equation

HRID 2089559 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[NH:17]C(=O)C)([O-:3])=[O:2].[OH-].[Na+].Cl.[Cl-].[NH4+]>CO>[N+:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[NH2:17])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 3828525N-(2-nitro-4-phenoxy-phenyl)acetamide

Product 1

HCID 51737522-Nitro-4-phenoxyanilineYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(2-nitro-4-phenoxy-phenyl)acetamide (0.67 g, 2.33 mmol) prepared in Step B was dissolved in methanol (5 mL), 6.0N sodium hydroxide (1.5 mL) was added thereto, and the mixture was stirred for 18 h at room temperature. After completion of the reaction, 6.0N aqueous hydrochloric acid solution (1.3 mL) and ammonium chloride solution (100 mL) were added thereto. The reaction mixture was extracted with ethyl acetate, dried over magnesium sulfate, and recrystallized from dichloromethane and hexane to give the title compound (521 mg, 2.12 mmol),

Workup

  1. additionwere added
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. customrecrystallized from dichloromethane and hexane

Sources & evidence

ORD record
ord-5afa791df78743a29c26813fe16f7258
Source dataset
uspto-grants-2013_05
Patent number
US08436038B2

Reaction notes

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