Ammonium Chloride → HCID 21246143, compound

HRID 620373Notes

Reaction equation

HRID 620373 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:10]1[C:11](=[O:17])[NH:12][N:13]=[CH:14][C:15]=1[Cl:16].[Cl-].[NH4+]>O1CCCC1>[Cl:16][C:15]1[CH:14]=[N:13][NH:12][C:11](=[O:17])[C:10]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 732474,5-Dichloro-3-hydroxypyridazineHCID 178418255HCID 178418255, compound

Product 1

HCID 21246143HCID 21246143, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyl magnesium bromide (prepared from bromobenzene (171 g), magnesium (38.8 g) and diethyl ether (1.6 l)) was slowly added to a stirred solution of 4,5-dichloro-3[2H]-pyridazinone (60 g) in tetrahydrofuran (1 l) cooled at water bath temperature. This mixture was stirred at room temperature for 30 minutes and hydrolysed with 20% ammonium chloride solution (800 ml) in the cold. The aqueous layer was extracted with diethyl ether and the combined organic extracts were washed with dilute hydrochloric acid, water, brine, dried (MgSO4) and evaporated under reduced pressure to give 5-chloro-4-phenyl-3[2H]-pyridazinone (55.13 g), m.p. 193°-5° C. on recrystallisation from ethyl acetate.

Workup

  1. temperaturecooled at water bath temperature
  2. extractionThe aqueous layer was extracted with diethyl ether
  3. washthe combined organic extracts were washed with dilute hydrochloric acid, water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4b02b8b49a234dbdb1bd95cf3ef70c18
Source dataset
uspto-grants-1989_04
Patent number
US04820819

Reaction notes

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