Acetylacetone → HCID 69307047, compound

HRID 860443Notes

Reaction equation

HRID 860443 reaction equation
[NH2:1][N:2]1[C:6]([CH2:7][CH3:8])=[CH:5][CH:4]=[C:3]1[C:9]([C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#[N:15])=O.[CH3:19][C:20](=O)[CH2:21][C:22](=[O:24])[CH3:23].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:22]([C:21]1[C:20]([CH3:19])=[N:1][N:2]2[C:6]([CH2:7][CH3:8])=[CH:5][CH:4]=[C:3]2[C:9]=1[C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#[N:15])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 31261AcetylacetoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 57444480HCID 57444480, compound

Product 1

HCID 69307047HCID 69307047, compoundYield 24.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-[(1-amino-5-ethyl-1H-pyrrol-2-yl)carbonyl]benzonitrile (200 mg) in toluene (6 mL) was added 2,4-pentanedione (837 mg) and p-toluenesulfonic acid monohydrate (32 mg) at ambient temperature. The reaction mixture was refluxed for 1 hour. The residue was purified by flash silica gel chromatography (silica gel, 80 mL) eluted with hexane-ethyl acetate=10-1 to give 3-(3-acetyl-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-4-yl)benzonitrile (63 mg, 24.8%) as an yellow solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. customThe residue was purified by flash silica gel chromatography (silica gel, 80 mL)
  3. washeluted with hexane-ethyl acetate=10-1

Sources & evidence

ORD record
ord-422c27119947496ea631f74da0456d3e
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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