Sodium Hydroxide → 7-Fluoro-8-methyl-5-nitro-3,4-dihydronaphthalen-1(2H)-one

HRID 355978Notes

Reaction equation

HRID 355978 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([CH2:11][CH2:12][CH2:13][C:14]([O:16]C)=O)=[CH:4][C:3]=1[CH3:18].[OH-].[Na+]>CO>[F:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:5]([CH2:11][CH2:12][CH2:13][C:14]2=[O:16])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22449411Methyl 4-(4-fluoro-5-methyl-2-nitrophenyl)butanoate

Product 1

HCID 224494067-Fluoro-8-methyl-5-nitro-3,4-dihydronaphthalen-1(2H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound obtained in (3) above (7.1 gm) was dissolved in 20 ml of methanol. To the solution was added 10 ml of 15% aqueous solution of sodium hydroxide and the mixture was stirred for 3 hours at room temperature. The reaction mixture was concentrated, acidified with concentrated hydrochloric acid, and extracted with chloroform. The chloroform layer was washed with water and saturated brine in this order and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was slowly added to 50 ml of polyphosphoric acid heated to 110° C. and stirred for 4.5 hours. After the addition of 100 ml of ice-water, the reaction product was extracted with ethyl acetate, washed with water, saturated sodium bicarbonate and saturated brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was subjected to silica gel column chromatography using a hexane-ethyl acetate (1:1) mixed solvent as an eluant to obtain fractions containing the target compound. The fractions were concentrated to produce 1.7 gm of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with chloroform
  3. washThe chloroform layer was washed with water and saturated brine in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. additionthe residue was slowly added to 50 ml of polyphosphoric acid
  7. temperatureheated to 110° C.
  8. stirringstirred for 4.5 hours
  9. additionAfter the addition of 100 ml of ice-water
  10. extractionthe reaction product was extracted with ethyl acetate
  11. washwashed with water, saturated sodium bicarbonate and saturated brine in this order
  12. dry with materialdried over anhydrous sodium sulfate
  13. customThe solvent was evaporated
  14. additionmixed solvent as an eluant
  15. customto obtain fractions
  16. additioncontaining the target compound
  17. concentrationThe fractions were concentrated

Sources & evidence

ORD record
ord-323cc22653e341a6853aa51a7faee7df
Source dataset
uspto-grants-1998_11
Patent number
US05834476

Reaction notes

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