Hydrochloric Acid → HCID 178526707, compound

HRID 1890323Notes

Reaction equation

HRID 1890323 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[F:12][C:13]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:14]=1[NH2:15].[OH-:21].[K+].Cl>C(O)C.CCOC(C)=O.O>[F:12][C:13]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:14]=1[NH:15][C:2]1[N:3]=[C:4]([OH:21])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 782782,3-DifluoroanilineHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 178526707HCID 178526707, compoundYield 26.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

2,6-Dichloro-3-nitropyridine (2.0 g, 10.4 mmol) and 2,3-difluoroaniline (2.5 g, 20.7 mmol) were taken up in ethanol (10.0 mL) and heated to 120° C. for 18 hours in a sealed tube. The solution was cooled in an ice bath, and the resulting precipitate was collected by vacuum filtration. The solid intermediate was dissolved in dioxane (12 mL) and 2 M aqueous potassium hydroxide solution (6.0 mL, 12.0 mmol) was added. The reaction mixture was heated to 80° C. for 18 h. After cooling to ambient temperature the mixture was diluted with EtOAc and H2O. The organic phase was discarded and the aqueous phase was acidified with 1 N HCl and extracted with EtOAc (2×). The organics were washed with brine, dried over MgSO4, filtered, and concentrated to give the title compound (743 mg). 1H NMR (400 MHz, CDCl3) δ ppm 6.52 (d, J=9.2 Hz, 1H), 6.80 (m, 1H), 6.97 (q, J=8.2 Hz, 1H), 7.06 (d, J=8.1 Hz, 1H), 8.22 (d, J=9.2 Hz, 1H), 10.09 (s, 1H).

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. filtrationthe resulting precipitate was collected by vacuum filtration
  3. dissolutionThe solid intermediate was dissolved in dioxane (12 mL)
  4. temperatureThe reaction mixture was heated to 80° C. for 18 h
  5. temperatureAfter cooling to ambient temperature the mixture
  6. extractionextracted with EtOAc (2×)
  7. washThe organics were washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-8f7c3918042a4a66a2be51daf2aef1b6
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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