Hydrazine hydrate (1:1) → HCID 59716612, compound

HRID 2224261Notes

Reaction equation

HRID 2224261 reaction equation
Cl[C:2]1[N:3]=[N:4][CH:5]=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.O.[NH2:22][NH2:23]>N1C=CC=CC=1>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:6]2[C:7]([C:8]3[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=3)=[C:2]([NH:22][NH2:23])[N:3]=[N:4][CH:5]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59716637HCID 59716637, compound

Product 1

HCID 59716612HCID 59716612, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-chloro-5-(4-fluorophenyl)4-(pyridin-4-yl)pyridazine (586 mg, 2.05 mmol) in pyridine (3 mL) at RT was added hydrazine monohydrate (0.6 mL). After addition, the reaction was heated to 100° C. for 3 h. After this time, the reaction mixture was cooled to RT. The reaction mixture was concentrated under reduced pressure and the residue was diluted with water. The resulting mixture was then extracted with EtOAc (3×50 mL). The combined organic layers were washed with saturted Nacl. The organic layer was dried (Na2SO4), filtered and concentrated. The resulting residue was triturated with EtOAc-hexane to give the title compound, 1-(5-(4-fluorophenyl)4-(pyridin-4-yl)pyridazin-3-yl)hydrazine (450 mg, 78%) as an off-white solid. LC/MS (method A): RT=1.10 min, (M+H)+=282.

Workup

  1. additionAfter addition
  2. temperatureAfter this time, the reaction mixture was cooled to RT
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with water
  5. extractionThe resulting mixture was then extracted with EtOAc (3×50 mL)
  6. washThe combined organic layers were washed with saturted Nacl
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting residue was triturated with EtOAc-hexane

Sources & evidence

ORD record
ord-1daecfd8ecdc43c38747d49c505133c3
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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