Hydrochloric Acid → HCID 178432236, compound

HRID 2423297Notes

Reaction equation

HRID 2423297 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.Cl.[CH3:11][C:12](=O)CC(=O)C.C([O-])(O)=O.[Na+]>CCO>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:11]([CH3:12])=[N:9][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31261AcetylacetoneHCID 1645844-Fluorobenzene-1,2-diamineHCID 516892Sodium Bicarbonate

Product 1

HCID 178432236HCID 178432236, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Under an N2 atmosphere, 4-fluorobenzene-1,2-diamine (5.00 g, 39.6 mmol) was suspended in EtOH (220 mL) and 5M HCl (160 mL) was added. The reaction was warmed to 50° C. and 2,4-pentandione (8.14 mL, 7.93 mmol) was added and the reaction was heated to reflux for 30 min. Upon cooling to room temperature, the reaction was neutralized with a saturated solution of NaHCO3(aq) and extracted with dichloromethane. The layers were separated and the aqueous layer was washed with additional dichloromethane (2×). The organics were then combined, dried (Na2SO4), filtered and concentrated in vacuo. The resulting solid was triturated with dichloromethane to afford the title compound. 1H NMR (400 MHz) (DMSO-d6) δ 7.43-7.19 (bm, 2H); 6.92 (bs, 1H); 2.44 (s, 3H).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 30 min
  3. temperatureUpon cooling to room temperature
  4. extractionextracted with dichloromethane
  5. customThe layers were separated
  6. washthe aqueous layer was washed with additional dichloromethane (2×)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resulting solid was triturated with dichloromethane

Sources & evidence

ORD record
ord-7809769529514faa89b94bf88607714c
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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