3-Benzyl-6-hydroxy-7-Methoxyquinazolin-4(3H)-one synthesis

6synthesis methods

Product Name:3-Benzyl-6-hydroxy-7-Methoxyquinazolin-4(3H)-one
CAS Number:808793-56-8
Molecular formula:C16H14N2O3
Molecular Weight:282.29

4(3H)-Quinazolinone, 6-(acetyloxy)-7-methoxy-3-(phenylmethyl)-

808793-55-7
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3-Benzyl-6-hydroxy-7-Methoxyquinazolin-4(3H)-one

808793-56-8
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Yield:808793-56-8 98%

Reaction Conditions:

Stage #1: 3-benzyl-3,4-dihydro-4-oxo-6-acetyloxy-7-methoxy-quinazolinewith water;sodium hydroxide in ethanol at 20 - 30; for 1 h;
Stage #2: with acetic acid in ethanol;water;Product distribution / selectivity;

Steps:

II.B

200 g 3-benzyl-3,4-dihydro-4-oxo-6-acetyloxy-7-methoxy-quinazoline are suspended in 200 ml of water and 1000 ml of ethanol. 300 ml 10N sodium hydroxide solution are added at ambient temperature and the mixture is heated to 30° C. for 1 hour. After the addition of 172 ml acetic acid and 2000 ml of water the mixture is stirred for 20 hours at ambient temperature. The precipitate is suction filtered, washed with water and acetone and dried at 60° C.Yield: 172.2 g (98% of theory)R_fvalue: 0.25 (silica gel, methylene chloride/ethanol=19:1)Mass spectrum (ESI⁺): m/z=283 [M+H]⁺

References:

US2009/306105,2009,A1 Location in patent:Page/Page column 5