Nitric Acid → 5-Nitro-2-oxindole

HRID 1272027Notes

Reaction equation

HRID 1272027 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[N+:11]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][C:2](=[O:10])[CH2:3]2)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 321710Oxindole

Product 1

HCID 2303665-Nitro-2-oxindoleYield 98%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-15 °C

Procedure

To a solution of oxindole (26 g) in 100 mL of concentrated sulfuric acid at −15° C. was added fuming nitric acid (8.4 mL) dropwise. Careful attention was paid to maintain the reaction temperature at −15° C. After the addition was complete, the reaction was stirred for 30 minutes and then poured into ice water. A yellow precipitate was formed which was isolated by filtration to provide 34 grams (98%) of 5-nitro oxindole.

Workup

  1. additionAfter the addition
  2. customA yellow precipitate was formed which
  3. customwas isolated by filtration

Sources & evidence

ORD record
ord-5912dedddfb344a2856b144e2a804a63
Source dataset
uspto-grants-2007_04
Patent number
US07208499B2

Reaction notes

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