Water → HCID 178518926, compound

HRID 1865824Notes

Reaction equation

HRID 1865824 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[C:6]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.CC#N.[OH2:25]>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[N:4][C:5]([OH:25])=[C:6]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6342AcetonitrileHCID 595155313,6-Dichloro-4-(4-chlorophenyl)-5-(pyridin-4-yl)pyridazine

Product 1

HCID 178518926HCID 178518926, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a round bottom flask was added 3,6-dichloro-4-(4-chlorophenyl)-5-(pyridin-4-yl)pyridazine (1.5 gm, 4.464 mmol), CH3CN (5 ml), water (1 ml) and LiOH monohydrate (0.938 gm, 22.32 mmol). The reaction was heated to 80° C. and stirred at this temperature for 4 hrs. After this time, the reaction was colled to rt and concentrated under reduced pressure. The residue was diluted with water (30 ml). The pH of the aqueous solution was adjusted to 7 with 1N HCl. The resulting solution was poured into a separatory funnel and extract with EtOAc (4×20 ml). The combined organic layers were washed with saturated aqueous NaCl (30 ml). The organic layer was then slurried with MgSO4 to remove excess water, filtered and concentrated to give a white solid residue. The residue was stirred in CH2Cl2 (10 ml) for 15 min. The solution was then filter and the solid was collected to give product 6-chloro-5-(4-chlorophenyl)-4-(pyridin-4-yl)pyridazin-3-ol as white solid (0.70 gm, 48% yield). HPLC retention time (method A) 1.332 min.

Workup

  1. customwas colled to rt
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with water (30 ml)
  4. additionThe resulting solution was poured into a separatory funnel
  5. extractionextract with EtOAc (4×20 ml)
  6. washThe combined organic layers were washed with saturated aqueous NaCl (30 ml)
  7. customto remove excess water
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a white solid residue
  11. filtrationThe solution was then filter
  12. customthe solid was collected

Sources & evidence

ORD record
ord-78b5ada592d5443c802e7d6b0117e62b
Source dataset
uspto-grants-2009_12
Patent number
US07629342B2

Reaction notes

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