Pyridine → HCID 22169697, compound

HRID 2224199Notes

Reaction equation

HRID 2224199 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=O)[NH:10][N:11]=[CH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.O=P(Cl)(Cl)[Cl:30]>C1(C)C=CC=CC=1>[Cl:30][C:9]1[N:10]=[N:11][CH:12]=[C:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 22169698HCID 22169698, compound

Product 1

HCID 22169697HCID 22169697, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4,5-Bis(4-chlorophenyl)pyridazin-3(2H)-one (16.5 g, 52.2 mmol) was suspended in toluene (50 mL). To the resultant solution was added pyridine (8.3 mL, 104.4 mmol), followed by the addition of POCl3 (14.3 mL, 156.6 mmol). The reaction mixture was placed in an oil bath preheated at 110° C. After 4 h, the reaction mixture was cooled to RT, then poured over 500 g ice to quench the excess POCl3. The dark mixture was extracted with EtOAc (2×300 mL). The combined organic layers were washed with water (500 mL), and filtered through a silica gel pad (˜50 g). The filtrate was concentrated under reduced pressure to give the title compound, 3-chloro-4,5-bis(4-chlorophenyl)pyridazine as a pale colored solid (16.0 g, 92%). MS: M+H=335. 1H NMR (CDCl3, 500 MHz): δ 9.24 (1H, s), 7.35 (2H, d, J=10 Hz), 7.26 (2H, d, J=10.0 Hz), 7.08-7.16 (4H, m).

Workup

  1. customThe reaction mixture was placed in an oil bath
  2. custompreheated at 110° C
  3. customto quench the excess POCl3
  4. extractionThe dark mixture was extracted with EtOAc (2×300 mL)
  5. washThe combined organic layers were washed with water (500 mL)
  6. filtrationfiltered through a silica gel pad (˜50 g)
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6ecd7f0b60eb4c41828cea004ba18497
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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