Water → 5-Fluoro-8-nitro-3,4-dihydronaphthalen-1(2H)-one

HRID 2186838Notes

Reaction equation

HRID 2186838 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12].[N+:13]([O-])([O-:15])=[O:14].[K+].O>S(=O)(=O)(O)O>[F:1][C:2]1[CH:11]=[CH:10][C:9]([N+:13]([O-:15])=[O:14])=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 24434Potassium NitrateHCID 154910385-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 224494055-Fluoro-8-nitro-3,4-dihydronaphthalen-1(2H)-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

14 gm of the compound prepared in (7) above was dissolved into 100 ml of concentrated sulfuric acid. After cooling the solution, a solution of 9.05 gm of potassium nitrate in 80 ml of concentrated sulfuric acid was added dropwise while maintaining the internal temperature below 5° C. The stirring was continued for a further 30 minutes. The resultant reaction mixture was poured into ice-cooled water and extracted with chloroform. The extract was washed with saturated aqueous solution of sodium bicarbonate, water, and saturated brine in this order, and dried over anhydrous sodium'sulfate. The solvent was evaporated and residue was recrystallized in methanol to obtain 9.15 gm of the title compound.

Workup

  1. temperatureAfter cooling the solution
  2. temperaturewhile maintaining the internal temperature below 5° C
  3. customThe resultant reaction mixture
  4. additionwas poured into ice-
  5. extractionextracted with chloroform
  6. washThe extract was washed with saturated aqueous solution of sodium bicarbonate, water, and saturated brine in this order
  7. dry with materialdried over anhydrous sodium'sulfate
  8. customThe solvent was evaporated
  9. customresidue was recrystallized in methanol

Sources & evidence

ORD record
ord-835981db21124a2cba16f0e927e9e95c
Source dataset
uspto-grants-2002_06
Patent number
US06407115B1

Reaction notes

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