4'-Methoxyacetophenone → HCID 73320030, compound

HRID 2063595Notes

Reaction equation

HRID 2063595 reaction equation
Cl.Cl.[NH:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([CH3:15])[N:6]=1)[NH2:4].C(N(CC)CC)C.[CH3:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)=O>C(O)C>[CH3:33][O:32][C:29]1[CH:30]=[CH:31][C:26]([C:24](=[N:4][NH:3][C:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=[C:7]([CH3:15])[N:6]=2)[CH3:23])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 74764'-MethoxyacetophenoneHCID 8471TriethylamineHCID 60209693HCID 60209693, compound

Product 1

HCID 73320030HCID 73320030, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-hydrazino-2-methylquinazoline dihydrochloride (100 mg, 0.40 mmol) and triethylamine (0.14 mL, 0.81 mmol) in ethanol (3 mL) was added 61 mg (0.4 mmol) of 4-methoxyacetophenone. The resultant solution was refluxed overnight and the resultant reaction mixture was absorbed directly on Si gel. Purification by automated Si gel chromatography (gradient 100% hexanes to 100% ethyl acetate) on the Flashmaster II was performed yielding 50 mg (36%) of the titled compound as a bright yellow solid. HPLC Purity: 91%.

Workup

  1. customthe resultant reaction mixture
  2. customwas absorbed directly on Si gel
  3. customPurification by automated Si gel chromatography (gradient 100% hexanes to 100% ethyl acetate) on the Flashmaster II

Sources & evidence

ORD record
ord-bbd457b8e4184f44b44a1541d6fbc912
Source dataset
uspto-grants-2012_10
Patent number
US08288398B2

Reaction notes

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