Sulfuric Acid → 5-Methoxyisatin

HRID 1057441Notes

Reaction equation

HRID 1057441 reaction equation
S(=O)(=O)(O)[OH:2].N(=[CH:8][C:9]([NH:11][C:12]1[CH:19]=[CH:18][C:15]([O:16][CH3:17])=[CH:14][CH:13]=1)=[O:10])O>O>[CH3:17][O:16][C:15]1[CH:14]=[C:13]2[C:12](=[CH:19][CH:18]=1)[NH:11][C:9](=[O:10])[C:8]2=[O:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 67107914-Methoxyisonitrosoacetanilide

Product 1

HCID 383335-MethoxyisatinYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Concentrated sulfuric acid (45 mL) containing 5 mL of water was warmed to 60° C. and 8.6 g of N-(2-hydroximinoacetyl)anisidine was added in one portion. The stirred mixture was heated to 93° C. for 10 minutes and then allowed to cool to room temperature. The mixture was poured into 500 g of ice and extracted 3 times with ethyl acetate. The combined extracts were dried over anhydrous sodium sulfate and concentrated to give 5.1 g (65% yield) of 5-methoxyisatin as a dark red solid.

Workup

  1. temperatureThe stirred mixture was heated to 93° C. for 10 minutes
  2. temperatureto cool to room temperature
  3. extractionextracted 3 times with ethyl acetate
  4. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2af550f044ba453c8bcfd12a079f2fbe
Source dataset
uspto-grants-2003_02
Patent number
US06514981B1

Reaction notes

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