HCID 86697017, compound → HCID 86697016, compound

HRID 1775531Notes

Reaction equation

HRID 1775531 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:6]([Cl:16])[C:7]=1[CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[OH:9]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:6]([Cl:16])[C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9]

Participants

4

Reactant 1

HCID 86697017HCID 86697017, compound

Product 1

HCID 86697016HCID 86697016, compoundYield 75.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of (3,5-dichloro-6-phenylpyridazin-4-yl)(phenyl)methanol (200 mg, 0.6 mmol), manganese dioxide (700 mg, 8 mmol) in dry toluene (20 mL) was heated at 115° C. for 3 h under Dean Stark conditions. The reaction mixture was cooled and filtered, and the residue was washed with CH2Cl2. The filtrate was concentrated in vacuo. The crude residue was purified by column chromatography (silica gel, gradient 10 to 20% ethyl acetate/isohexane) yielding (3,5-dichloro-6-phenylpyridazin-4-yl)(phenyl)methanone as a solid (150 mg).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. washthe residue was washed with CH2Cl2
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe crude residue was purified by column chromatography (silica gel, gradient 10 to 20% ethyl acetate/isohexane)

Sources & evidence

ORD record
ord-d23a4a0de19b4cef937999c009f74c82
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

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