ChemicalBook CAS DataBase List 6-Hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one

6-Hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one synthesis

8synthesis methods

Product Name:6-Hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one
CAS Number:179688-52-9
Molecular formula:C9H8N2O3
Molecular Weight:192.17

6,7-Dimethoxy-3,4-dihydroquinazoline-4-one

13794-72-4

6-Hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one

179688-52-9

General procedure for the synthesis of 6-hydroxy-7-methoxyquinazolin-4-one from 6,7-dimethoxyquinazolin-4-one: 1. 3.06 g of 6,7-dimethoxyquinazolin-4-one was dissolved in 20 mL of methanesulfonic acid. 2. 2.66 g of L-methionine was added to the above solution and the reaction was stirred at 100 °C for 22 hours. 3. Upon completion of the reaction, ice was added to the reaction mixture and neutralized with 40% aqueous sodium hydroxide solution to pH neutral to promote crystallization of the product. 4. The solid product was collected by filtration under reduced pressure, washed with water and subsequently air dried to afford 6-hydroxy-7-methoxyquinazolin-4-one (2.67 g, 94% yield). Product characterization data: 1H-NMR (300MHz, DMSO-d6) δ 11.94 (s, 1H), 9.81 (s, 1H), 7.92 (d, J=Hz, 1H), 7.39 (s, 1H), 7.11 (s, 1H), 3.91 (s, 3H).

13794-72-4
290 suppliers
$8.00/1g

179688-52-9
239 suppliers
$6.00/1g

Yield:179688-52-9 94%

Reaction Conditions:

with methanesulfonic acid;L-methionine at 100; for 22 h;

Steps:

1.1-2
( 1 -2) 6-hydroxy-7-methoxyquinazolin-4(3H)-one; 3.06 g of the compound obtained in (1-1) was diluted with 20 mi of methanesulfonic acid. 2.66 g of /--methionine was added to the resulting solution and stirred at 100 ^°C for 22 hours. Ice was added to the reaction mixture and neutralized with 40% aqueous sodium hydroxide to induce the crystallization of the product. The solid was filtered under a reduced pressure, washed with water, and air-dried to obtain the title compound (2.67 g, 94%).¹H-NMR (300MHz, DMSO-d₆) δ 11.94 (s, IH), 9.81 (s, IH), 7.92 (_?, IH), 7.39 (s, IH), 7.11 (s, IH), 3.91 (s, 3H).

References:

HANMI PHARM. CO., LTD. WO2008/150118, 2008, A2 Location in patent:Page/Page column 21

FullText