Acetic Acid → HCID 18977156, compound

HRID 1939929Notes

Reaction equation

HRID 1939929 reaction equation
Br.C(O)(=O)C.C(O)(=O)C.[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]([CH3:29])[CH:23]([CH3:28])[C:24](=[O:27])[NH:25][N:26]=2)=[CH:17][CH:16]=1>CS(C)=O>[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[C:22]([CH3:29])=[C:23]([CH3:28])[C:24](=[O:27])[NH:25][N:26]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 18977185HCID 18977185, compoundHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 18977156HCID 18977156, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

44 ml of a 25% hydrogen bromide-acetic acid solution was added to 44 ml of an acetic acid solution containing 2.20 g of 6-[4-(4-aminobutyl)phenyl]-4,5-dihydro-4,5-dimethylpyridazin-3(2H)-one, and the mixture was stirred at room temperature for 5 minutes. Then, 0.75 ml of dimethylsulfoxide was added to the mixture, and the resulting mixture was stirred for 6 hours. The solvent was removed, and the residue was dissolved in 150 ml of water. The solution was made alkaline with ammonia and extracted with chloroform. After the chloroform layer was washed with water and dried, the solvent was removed. The residue was purified by silica gel column chromatography (eluent:chloroform-methanol-28 % aqueous ammonia (10:1:0.1)) to obtain 1.52 g of 6-[4-(4-aminobutyl)phenyl]-4,5-dimethylpyridazin-3(2H)-one.

Workup

  1. stirringthe resulting mixture was stirred for 6 hours
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in 150 ml of water
  4. extractionextracted with chloroform
  5. washAfter the chloroform layer was washed with water
  6. customdried
  7. customthe solvent was removed
  8. customThe residue was purified by silica gel column chromatography (eluent:chloroform-methanol-28 % aqueous ammonia (10:1:0.1))

Sources & evidence

ORD record
ord-44dd5fdde4b34899a1f1b4ebe843176b
Source dataset
uspto-grants-1997_12
Patent number
US05698554

Reaction notes

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