Hydrochloric Acid → HCID 12924785, compound

HRID 2367873Notes

Reaction equation

HRID 2367873 reaction equation
[CH:1]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]2[C:10]([C:12]3[CH:17]=[C:16]([C:18]([OH:20])=[O:19])[CH:15]=[CH:14][C:13]=3[C:3]=2[CH:2]=1)=O.[OH-].[Na+].O.NN.Cl>C(O)COCCO.O>[CH:17]1[C:12]2[CH2:10][C:4]3[C:3](=[CH:2][CH:1]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=3)[C:13]=2[CH:14]=[CH:15][C:16]=1[C:18]([OH:20])=[O:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 27589459-Oxo-9H-fluorene-2,7-dicarboxylic acid

Product 1

HCID 12924785HCID 12924785, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8117Diethylene GlycolSolvent

Procedure

In an argon-purged flask, 9-fluorenone-2,7-dicarboxylic acid (10.0 g, 0.037 mol) was suspended in diethylene glycol (75 mL). The flask was placed in a room temperature oil bath then NaOH (6.2 g, 0.155 mol) and an 80% solution of hydrazine hydrate (7.4 mL, 0.12 mol) were added successively. The reaction mixture was slowly heated to 110 C and refluxed for approximately four hours. The reaction mixture was cooled, carefully poured into water and acidified to pH 2 with concentrated HCl. The product was filtered and washed with water. Product was dissolved in warm NaOH solution (0.5M, warm) and precipitated by acidification to pH 2 with HCl. The product was filtered and washed with water. Product was an yellow solid (9.0 g, 96%). 1H-NMR (d6-DMSO): δ (ppm) 8.2 (s, 2H, Ar); 8.1 (m, 2H, Ar); 8.0 (m, 2H, Ar); 4.1 (s, 2H, CH2).

Workup

  1. customIn an argon-purged flask
  2. customwas placed in a room temperature
  3. temperatureThe reaction mixture was slowly heated to 110 C
  4. temperaturerefluxed for approximately four hours
  5. temperatureThe reaction mixture was cooled
  6. filtrationThe product was filtered
  7. washwashed with water
  8. dissolutionProduct was dissolved in warm NaOH solution (0.5M, warm)
  9. customprecipitated by acidification to pH 2 with HCl
  10. filtrationThe product was filtered
  11. washwashed with water

Sources & evidence

ORD record
ord-99456cd0a55c4fdf83cc6d6adf7bd623
Source dataset
uspto-grants-2014_04
Patent number
US08703115B2

Reaction notes

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