Sulfuric Acid → HCID 15345813, compound

HRID 1385199Notes

Reaction equation

HRID 1385199 reaction equation
[NH2:1][C:2]1[C:3](=[O:14])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1Cl)=[CH:8][CH:7]=[CH:6][CH:5]=2.[F:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=[O:20].S(=O)(=O)(O)O.CCOCC>[N+](C1C=CC=CC=1)([O-])=O>[O:14]=[C:3]1[C:2]2[N:1]=[C:19]([C:18]3[CH:22]=[CH:23][CH:24]=[C:16]([F:15])[CH:17]=3)[O:20][C:11]=2[C:10](=[O:13])[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 177482-Amino-3-chloro-1,4-naphthoquinoneHCID 743763-Fluorobenzoyl chloride

Product 1

HCID 15345813HCID 15345813, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

To a solution of 5.00 g (24 mmol) of 2-amino-3-chloro-1,4-dihydro-1,4-dioxonaphthalene in 50 mL of nitrobenzene, 14.6 mL (120 mmol) of 3-fluorobenzoic acid chloride are added; after 5 min of stirring, 0.50 mL of concentrated sulfuric acid is then added with protection from light. After 24 h of reflux and complete cooling, 200 mL of ether are added to the reaction mixture. The precipitate formed is filtered, then redissolved in 200 mL of dichloromethane, to which 100 mL of a glacial sodium hydroxide solution are added. After 6 h of stirring at this temperature, the organic phase is extracted, washed several times with water and dried over calcium chloride. The solid obtained after evaporation of the solvent is purified on a medium-pressure column (support: silica; conditioning heptane; eluant: dichloromethane/heptane, 50/50). The yellow crystals so obtained are uncolored and recrystallized in a dichloromethane/heptane mixture (volume/volume) to produce 0.50 g of 4,9-dihydro-4,9-dioxo-2-(3-fluorophenyl)-naphtho[2,3-d]oxazole in the form of yellow crystals.

Workup

  1. temperatureAfter 24 h of reflux
  2. customThe precipitate formed
  3. filtrationis filtered
  4. dissolutionredissolved in 200 mL of dichloromethane, to which 100 mL of a glacial sodium hydroxide solution
  5. additionare added
  6. stirringAfter 6 h of stirring at this temperature
  7. extractionthe organic phase is extracted
  8. washwashed several times with water
  9. dry with materialdried over calcium chloride
  10. customThe solid obtained
  11. customafter evaporation of the solvent
  12. customis purified on a medium-pressure column (support: silica; conditioning heptane; eluant: dichloromethane/heptane, 50/50)
  13. customThe yellow crystals so obtained
  14. customrecrystallized in a dichloromethane/heptane mixture (volume/volume)

Sources & evidence

ORD record
ord-384762032c62428e9441e44058c6b133
Source dataset
uspto-grants-2001_07
Patent number
US06262095B1

Reaction notes

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