Hydrochloric Acid → HCID 10998901, compound

HRID 1764635Notes

Reaction equation

HRID 1764635 reaction equation
[N+](C1C=C(C=CC=1)C(C(C)CC#N)=O)([O-])=O.Cl.[N+:18]([C:21]1[CH:22]=[C:23]([CH:32]=[CH:33][CH:34]=1)[C:24]([CH:26]([CH3:31])[CH2:27][C:28](O)=[O:29])=O)([O-:20])=[O:19].O.[NH2:36][NH2:37]>C(O)C>[CH3:31][CH:26]1[C:24]([C:23]2[CH:32]=[CH:33][CH:34]=[C:21]([N+:18]([O-:20])=[O:19])[CH:22]=2)=[N:37][NH:36][C:28](=[O:29])[CH2:27]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 22768930HCID 22768930, compoundHCID 22768939HCID 22768939, compound

Product 1

HCID 10998901HCID 10998901, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 28 g. portion of 3-(m-nitrobenzoyl)butyronitrile [prepared as described in J. Org. Chem., Vol. 38, No. 23, 4044-4048 (1973)] is added to one liter of 6N hydrochloric acid and is stirred at reflux for one hour using a magnetic stirrer and a heating mantle. The reaction mixture is cooled and extracted with methylene chloride. The organic layer is separated and extracted with saturated sodium bicarbonate. The bicarbonate layer is added dropwise to a stirred cold hydrochloric acid solution and the resulting solid is kept cold in ice then is filtered and air dried to afford 27.24 g. of 3-m-nitrobenzoyl butyric acid as a white solid. The entire amount of the preceding compound is mixed with 12.8 ml. of 99% hydrazine hydrate in 140 ml. of ethyl alcohol and is stirred at reflux for 3 hours. A solid begins to appear after about half an hour. The reaction mixture is cooled in an ice bath and the resulting solid is filtered and air dried to afford the compound 4,5-dihydro-5 -methyl-6-(m-nitrophenyl)-3(2H)-pyridazinone as white to light yellow crystals.

Workup

  1. temperatureat reflux for one hour
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with methylene chloride
  4. customThe organic layer is separated
  5. extractionextracted with saturated sodium bicarbonate
  6. additionThe bicarbonate layer is added dropwise to a stirred cold hydrochloric acid solution
  7. filtrationthen is filtered
  8. customair dried
  9. customto afford 27.24 g
  10. additionThe entire amount of the preceding compound is mixed with 12.8 ml
  11. temperatureat reflux for 3 hours
  12. waitto appear after about half an hour
  13. temperatureThe reaction mixture is cooled in an ice bath
  14. filtrationthe resulting solid is filtered
  15. customair dried

Sources & evidence

ORD record
ord-a6313879bc3e4ba29f224c68d37696ed
Source dataset
uspto-grants-1978_09
Patent number
US04117130

Reaction notes

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