Phosphorus oxychloride → HCID 58326546, compound

HRID 2197410Notes

Reaction equation

HRID 2197410 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[N:14]=[N:13][C:12](O)=[CH:11][CH:10]=1.O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:12]1[N:13]=[N:14][C:9]([C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:8])=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178424774HCID 178424774, compound

Product 1

HCID 58326546HCID 58326546, compound

Conditions

Temperature
80 °C

Procedure

A mixture of 6-(2,6-dimethyl-phenyl)-pyridazin-3-ol in POCl3 is heated at 80° C. for 2 h. The volatile material is evaporated under reduced pressure and the residue is partitioned between EtOAc and diluted NaOH aqueous solution. The organic layer is separated and the aqueous layer is extracted with EtOAc once. The combined organic extract is washed with brine, dried and concentrated in vacuo. The crude product is purified by flash column (Hexanes/EtOAc 4:1) to give 3-chloro-6-(2,6-dimethyl-phenyl)-pyridazine. 1H NMR: (CDCl3) 7.59 (d, 1H), 7.38 (d, 1H), 7.25 (m, 1H), 7.14 (d, 2H), 2.06 (s, 6H).

Workup

  1. customThe volatile material is evaporated under reduced pressure
  2. customthe residue is partitioned between EtOAc and diluted NaOH aqueous solution
  3. customThe organic layer is separated
  4. extractionthe aqueous layer is extracted with EtOAc once
  5. extractionThe combined organic extract
  6. washis washed with brine
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe crude product is purified by flash column (Hexanes/EtOAc 4:1)

Sources & evidence

ORD record
ord-f6f763e8ead9480fb409ecd3a5d8b0b0
Source dataset
uspto-grants-2012_12
Patent number
US08338591B2

Reaction notes

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