Nitric Acid → HCID 21713585, compound

HRID 369726Notes

Reaction equation

HRID 369726 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:12]([O-:15])(=[O:14])=[O:13])=[CH:4][CH:3]=1.[K+].[N+:17]([O-])([OH:19])=[O:18]>C(OCC)C>[Br:1][C:2]1[C:11]2[C:6](=[C:7]([N+:17]([O-:19])=[O:18])[CH:8]=[CH:9][CH:10]=2)[C:5]([S:12]([OH:15])(=[O:13])=[O:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 23713432HCID 23713432, compound

Product 1

HCID 21713585HCID 21713585, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-15 °C

Procedure

Potassium 4-bromo-naphthalene-1-sulfonate (1.38 g, 4.24 mmol) was added portionwise over 20 minutes to 90% nitric acid (2 mL), which was cooled in a methanol/ice bath to approximately -15° C. After 1.5 hours, the mixture was placed in a refrigerator for 20 hours. Diethyl ether (20 mL) was added and the precipitated solid was filtered, washed with ether (100 mL) and isopropanol (20 mL), and dried under a stream of nitrogen to give the title compound as an approximately 4:1 mixture of the 5- and 8-nitro isomers (1.25 g).

Workup

  1. waitthe mixture was placed in a refrigerator for 20 hours
  2. filtrationthe precipitated solid was filtered
  3. washwashed with ether (100 mL) and isopropanol (20 mL)
  4. customdried under a stream of nitrogen

Sources & evidence

ORD record
ord-0842eb3712c3463185535915c0573329
Source dataset
uspto-grants-2000_10
Patent number
US06140318

Reaction notes

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