Ethyl orthopropionate → 7-Bromo-2-ethyl-3-methyl-4(3H)-quinazolinone

HRID 601662Notes

Reaction equation

[C:1](OCC)(OCC)(OCC)[CH2:2]C.[CH3:13][NH:14][C:15](=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=1[NH2:23].[C:25](=O)(O)[O-].[Na+]>C(O)(=O)C>[Br:22][C:19]1[CH:18]=[C:17]2[C:16]([C:15](=[O:24])[N:14]([CH3:25])[C:13]([CH2:1][CH3:2])=[N:23]2)=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

1.5 ml of triethyl orthopropionate and 30 μL of acetic acid were added to 1 ml solution of N-methyl-2-pyrolidine with 796 mg of N-methyl-2-amino4-bromobenzamide, and the mixture was stirred at 100° C. for 1 hour. Saturated sodium bicarbonate aqueous solution was added to the reaction solution, and extracted with ether. Ether layer was washed with saturated saline solution, and dried with anhydrous magnesium sulfate. After distilling out the solvents under reduced pressure, the residues were separated and purified by silicagel column chromatography (hexane/ethyl acetate=4/1), to obtain 653 mg of the above compound as a colorless solid.

Workup

extractionextracted with ether
washEther layer was washed with saturated saline solution
dry with materialdried with anhydrous magnesium sulfate
distillationAfter distilling out the solvents under reduced pressure
customthe residues were separated
custompurified by silicagel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-3811d9dc763d4ad09721fce0128ad35d
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902369B2

Reaction notes

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