Ammonium nitrate → 1-Acetyl-5-nitroindolin-2-one

HRID 24796Notes

Reaction equation

HRID 24796 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C:5]1=[O:13])(=[O:3])[CH3:2].[N+:14]([O-])([O-:16])=[O:15].[NH4+]>S(=O)(=O)(O)O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:14]([O-:16])=[O:15])=[CH:10][CH:11]=2)[CH2:6][C:5]1=[O:13])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 22985Ammonium nitrateHCID 3237191-Acetylindolin-2-one

Product 1

HCID 28393291-Acetyl-5-nitroindolin-2-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

17.5 g (0.10 mol) of 1-acetyl-2-indolinone are dissolved in 100 ml of conc. sulphuric acid and at −10° C. 8.8 g (0.11 mol) of ammonium nitrate are added batchwise and stirred for 15 minutes. The reaction is poured onto ice water, suction filtered and washed with water. The residue is distributed in ethyl acetate/water, the combined organic extracts are dried and concentrated by evaporation.

Workup

  1. additionThe reaction is poured onto ice water, suction
  2. filtrationfiltered
  3. washwashed with water
  4. customthe combined organic extracts are dried
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-876a4116b49845fd9885779f56dd4f70
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Reaction notes

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