Sodium Hydroxide → HCID 18785595, compound

HRID 1107815Notes

Reaction equation

HRID 1107815 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][C:7]1[N:16]=[C:10]2[C:11](=O)[NH:12][NH:13][CH:14]=[C:9]2[C:8]=1[CH3:17].[OH-].[Na+]>>[Cl:3][C:11]1[N:12]=[N:13][CH:14]=[C:9]2[C:8]([CH3:17])=[C:7]([CH3:6])[NH:16][C:10]=12

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178432363HCID 178432363, compound

Product 1

HCID 18785595HCID 18785595, compound

Procedure

45 ml of phosphorus oxychloride were added to 3.35 g (0.021 mole) of 2,3-dimethyl-6,7-dihydropyrrolo[2,3-d]pyridazin-7-one and the mixture was heated under reflux for 2 hours. After completion of the reaction, the reaction mixture was slowly poured into ice-water and the aqueous mixture was neutralized with an aqueous solution of sodium hydroxide. The precipitated yellow solids were collected by filtration and washed well with water. The solids were dissolved in dichloromethane and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography through silica gel using a 15:1 mixture of chloroform and methanol as an eluent to give 2.39 g of 7-chloro-2,3-dimethylpyrrolo[2,3-d]pyridazine as a pale yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customAfter completion of the reaction
  4. filtrationThe precipitated yellow solids were collected by filtration
  5. washwashed well with water
  6. dissolutionThe solids were dissolved in dichloromethane
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by column chromatography through silica gel using
  10. additiona 15:1 mixture of chloroform and methanol as an eluent

Sources & evidence

ORD record
ord-535e88c42ad84cc0bed2c0a1ce420094
Source dataset
uspto-grants-2000_05
Patent number
US06063782

Reaction notes

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