Sulfuric Acid → 2-Amino-5-nitrobenzene-1,3-diol

HRID 647222Notes

Reaction equation

HRID 647222 reaction equation
S([O:11][C:12]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[C:14]([O:15]S(C2C=CC(C)=CC=2)(=O)=O)[C:13]=1[NH:32]C(=O)C)(C1C=CC(C)=CC=1)(=O)=O.S(=O)(=O)(O)O.[OH-].[Na+].C(=O)(O)[O-].[Na+]>>[NH2:32][C:13]1[C:14]([OH:15])=[CH:26][C:27]([N+:29]([O-:31])=[O:30])=[CH:28][C:12]=1[OH:11]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 714103122-Acetamido-5-nitroresorcinol ditosylate

Product 1

HCID 204858732-Amino-5-nitrobenzene-1,3-diolYield 86.4%

Procedure

2-Acetamido-5-nitroresorcinol ditosylate (9.0 g, 0.017 mole) was added to cold sulfuric acid (25 ml, at or below 10° C.). The mixture was stirred cold an additional fifteen minutes and then at ambient temperature for 1.5 hours. The mixture was then poured into 250 ml ice water and sodium hydroxide (30 g, 0.75 mole) was slowly added. The mixture was then treated with sodium bicarbonate until it was no longer acidic, and aqueous solution was extracted twice with ethyl acetate (150 ml). The extracts were combined, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to yield a light yellow solid (2.5 g, 86.2 percent). TLC showed the product was pure.

Workup

  1. additionwas slowly added
  2. extractionaqueous solution was extracted twice with ethyl acetate (150 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a7f269829a454e719b01220386c8464b
Source dataset
uspto-grants-1983_10
Patent number
US04407930

Reaction notes

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