Hydrochloric Acid → 5-[N-Benzyl-N-(3-hydroxypropyl)amino]-4-chloro-2-methyl-3(2H)-pyridazinone

HRID 394450Notes

Reaction equation

HRID 394450 reaction equation
[Cl:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[N:5]=[CH:6][C:7]=1Cl.[CH2:11]([NH:18][CH2:19][CH2:20][CH2:21][OH:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>O>[CH2:11]([N:18]([C:7]1[CH:6]=[N:5][N:4]([CH3:9])[C:3](=[O:10])[C:2]=1[Cl:1])[CH2:19][CH2:20][CH2:21][OH:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784483-(Benzylamino)propanolHCID 1204623(2H)-Pyridazinone, 4,5-dichloro-2-methyl-

Product 1

HCID 181764695-[N-Benzyl-N-(3-hydroxypropyl)amino]-4-chloro-2-methyl-3(2H)-pyridazinoneYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 11.48 g (64,1 mmol) of 4,5-dichloro-2-methyl-3(2H)-pyridazinone and 31.84 g (193.0 mmol) of 3-(N-benzylamino)propanol in 250 ml of water is boiled for 25 hours while stirring. The mixture is cooled, its pH is set with concentrated hydrochloric acid to 3 and it is extracted with 2×400 ml of ethyl acetate. The organic phase is dried and evaporated, 10 ml of ethyl acetate are added to the evaporation residue, then it is left to stand overnight at −10° C. The precipitated crystals are filtered and washed with ethyl acetate and then with diethyl ether. In this way 10.60 g (54%) of the title compound are obtained with a melting point of 94-95° C.

Workup

  1. temperatureThe mixture is cooled
  2. extractionis extracted with 2×400 ml of ethyl acetate
  3. customThe organic phase is dried
  4. customevaporated
  5. addition10 ml of ethyl acetate are added to the evaporation residue
  6. waitit is left
  7. filtrationThe precipitated crystals are filtered
  8. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-838347e9268b46adbbb3b2e4df592739
Source dataset
uspto-grants-2003_08
Patent number
US06602865B1

Reaction notes

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