Hydrochloric Acid → 2-Nitro-4-phenoxyaniline

HRID 1466471Notes

Reaction equation

HRID 1466471 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-22c7770506c84b809f480e95ed97e81e
Source dataset
uspto-grants-2015_04
Patent number
US09000028B2

Reaction notes

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