Sodium Dithionite → 4-(4-Nitrophenoxy)benzenamine

HRID 1294055Notes

Reaction equation

HRID 1294055 reaction equation
[O-]S(S([O-])=O)=O.[Na+].[Na+].C([NH:12][C:13]1[CH:29]=[CH:28][C:16]([O:17][C:18]2[CH:19]=[CH:20][C:21]([N+:25]([O-:27])=[O:26])=[C:22]([CH:24]=2)N)=[CH:15][CH:14]=1)(=O)C>CCO.O>[N+:25]([C:21]1[CH:22]=[CH:24][C:18]([O:17][C:16]2[CH:28]=[CH:29][C:13]([NH2:12])=[CH:14][CH:15]=2)=[CH:19][CH:20]=1)([O-:27])=[O:26]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 13705240N-[4-(3-Amino-4-nitrophenoxy)phenyl]acetamide2×

Product 1

HCID 802514-(4-Nitrophenoxy)benzenamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Na2S2O4 (28.2 g, 160 mmol) was added to a solution of 5-(4-Acetamidophenoxy)-2-nitroaniline (Intermediate 1) (13.7 g, 48 mmol) in EtOH (600 ml) and H2O (150 ml). The yellow mixture was refluxed with vigorous stirring until the color disappeared. After cooling, the mixture was washed with brine and the product was extracted with AcOEt. The AcOEt layer was dried over MgSO4, filtered and evaporated to give intermediate 2 as a brown film (10.2 g, 83%): MS m/e 258 (M+1).

Workup

  1. temperatureThe yellow mixture was refluxed
  2. temperatureAfter cooling
  3. washthe mixture was washed with brine
  4. extractionthe product was extracted with AcOEt
  5. dry with materialThe AcOEt layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-22e04f6d98614adc8722751ee30a6b65
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

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