Ethanol Synthesis Lab Report

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(Un) substituted-2-phenyl-4H-3, 1-benzoxazin-4 one (1, 2) was converted to 3-amino-2-phenylquinazolin-4(3H)-one and its substituted analog under reflux for 6-7 hr with hydrazine monohydrate in ethanol. The concentrated solution was poured into ice cold water to obtain a solid product. The obtained solid was washed with water, filtered, dried and recrystallized from ethanol1.
Synthesis of 3-(benzylideneamino)-2-phenylquinazolin-4-(3H)-one 5 (a-j)
A mixture of 3-amino-2-phenyl-3H-quinazoline-4-one as well as its substituted analogs (3-4) and the appropriate aromatic aldehydes dissolved in ethanol (50 mL) containing few drops of glacial acetic acid were heated under reflux for 7-8 hr. The solution was cooled and the precipitated solid was obtain, filtered, and washed with water, dried in vacuum and recrystallized from ethanol 2, 3.
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Anal.calcd. for C23H19IN4O: C, 55.81; H, 3.87; N, 11.33. Found: C, 54.83; H, 3.91; N, 11.21.
General procedure for the synthesis of N-benzylidene-4-chloro-2-phenylquinazolin-3-(4H)-amine 6(a-j)
A solution of compound 5(a-j) and DIPEA (mole ratio 1: 2) in anhydrous toluene was refluxed for 2 hr. After cooling to room temperature, POCl3 was added and heating was continued for further 4-6 hr. The solution was cooled and diluted with ethyl acetate; organic layer was separated and concentrated to obtain the solid desired compounds, filtered, washed with water, dried in vacuum and recrystallized with carbinol.
N-Benzylidene-4-chloro-2-phenylquinazolin-3-(4H)-amine

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