Nitric Acid → 1,3-dihydro-4-iodo-5-nitro-2H-indol-2-one

HRID 428648Notes

Reaction equation

HRID 428648 reaction equation
[N+:1]([O-:4])(O)=[O:2].[I:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH2:8][C:9](=[O:15])[NH:10]2>S(=O)(=O)(O)O>[I:5][C:6]1[C:14]([N+:1]([O-:4])=[O:2])=[CH:13][CH:12]=[C:11]2[C:7]=1[CH2:8][C:9](=[O:15])[NH:10]2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 109232254-Iodo-1,3-dihydro-2H-indol-2-one

Product 1

HCID 120188061,3-dihydro-4-iodo-5-nitro-2H-indol-2-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A mixture of concentrated sulfuric acid (0.73 mL) and concentrated nitric acid (0.14 mL) was added slowly to a solution of 1,3-dihydro-4-iodo-2H-indol-2-one (0.5 g, 1.93 mmol) (see Fukuyama, supra) in concentrated sulfuric acid (6 mL) at −5° C., with stirring. The mixture was stirred for an additional 15 min at −5° C., then poured onto ice. After standing for 1 h, solid was collected by filtration and washed with water, and dried in a vacuum oven to give 1,3-dihydro-4-iodo-5-nitro-2H-indol-2-one. (Yield 0.46 g, 78%).

Workup

  1. stirringThe mixture was stirred for an additional 15 min at −5° C.
  2. additionpoured onto ice
  3. filtrationsolid was collected by filtration
  4. washwashed with water
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-c100dde0ef3f4c95bbb62ed8f0391365
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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