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

HRID 382011Notes

Reaction equation

HRID 382011 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br: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>[Br: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 27631904-bromo-2,3-dihydro-1H-indol-2-one

Product 1

HCID 120188074-bromo-5-nitro-2,3-dihydro-1H-indol-2-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A mixture of concentrated sulfuric acid (3.6 mL) and concentrated nitric acid (0.7 mL) was added slowly to a solution of 4-bromo-1,3-dihydro-2H-indol-2-one (2 g, 9.48 mmol) (see Kosuge et al., supra) in concentrated sulfuric acid (20 mL) at −5° C. with stirring. The mixture was stirred for an additional 1 h at −5° C. then poured into ice. After standing for 1 h, precipitate formed was collected by filtration and washed with water, and dried in a vacuum oven to give the above product. (Yield 2.33 g, 96%).

Workup

  1. stirringThe mixture was stirred for an additional 1 h at −5° C.
  2. additionthen poured into ice
  3. customprecipitate formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried in a vacuum oven
  7. customto give the above product

Sources & evidence

ORD record
ord-47e8c85907da4127a2c78504bace5b4b
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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