Hydrochloric Acid → HCID 21246146, compound

HRID 2118533Notes

Reaction equation

HRID 2118533 reaction equation
[CH3:1][CH:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH2:15][CH:16]([OH:23])[CH2:17][NH:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N:6][NH:5][C:4](=[O:24])[CH2:3]1.[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O.[Na+].Cl>[OH-].[Na+].O>[CH3:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH2:15][CH:16]([OH:23])[CH2:17][NH:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[N:6][NH:5][C:4](=[O:24])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 31389Sodium 3-nitrobenzenesulfonateHCID 21246159HCID 21246159, compound

Product 1

HCID 21246146HCID 21246146, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

5-Methyl-6-[2-(3-t-butylamino-2-hydroxypropoxy)phenyl]-4,5-dihydro-3[2H]-pyridazinone (preparable from British Patent Specification No. 1488330) (1.3 g) and sodium 3-nitrobenzene sulphonate (0.88 g) were mixed in aqueous sodium hydroxide (0.38 g in 50 ml) and stirred under reflux for 3 hours. The reaction mixture was cooled, neutralised with hydrochloric acid and evaporated under reduced pressure to afford a residue. This was dissolved in water, on standing a solid precipitated which was filtered off (recovered sodium 3-nitrobenzene sulphonate). The filtrate was shaken with chloroform whereupon a white solid precipitated which was collected and dried to afford the title compound (0.4 g).

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureThe reaction mixture was cooled
  3. customevaporated under reduced pressure
  4. customto afford a residue
  5. customprecipitated which
  6. filtrationwas filtered off
  7. custom(recovered sodium 3-nitrobenzene sulphonate)
  8. stirringThe filtrate was shaken with chloroform whereupon a white solid
  9. customprecipitated which
  10. customwas collected
  11. customdried

Sources & evidence

ORD record
ord-3cbe0039ba5543f694f13fb82b68ba7e
Source dataset
uspto-grants-1987_07
Patent number
US04678786

Reaction notes

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