Process for preparation of 6, 7-bis(2-methoxyethoxy) quinazolin-4-one
AssigneeUbe Industries, Ltd.
InventorsShigeyoshi Nishino, Kenji Hirotsu, Hidetaka Shima, Hiroyuki Oda, Shinobu Suzuki
Life of this patent
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Abstract
6,7-Bis(2-methoxyethoxy)quinazolin-4-one of formula (5) useful in synthesis of an anti-cancer drug can be prepared by a reaction of ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate of formula (4) with an orthoformic acid in the presence of an ammonium acetate:
Claims6
A process for preparation of 6,7-bis(2-methoxyethoxy)quinazolin-4-one, which comprises causing a reaction of ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate with an orthoformic ester in the presence of ammonium acetate.
A process for preparation of 6,7-bis(2-methoxyethoxy)quinazolin-4-one, which comprises the steps in order of:
- causing a reaction of ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate with hydrogen in the presence of a metallic catalyst to prepare ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate;
- and causing a reaction of the ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate with an orthoformic ester in the presence of ammonium acetate to prepare 6,7-bis(2-methoxyethoxy)quinazolin-4-one.
A process for preparation of 6,7-bis(2-methoxyethoxy)quinazolin-4-one, which comprises the steps in order of:
- causing a reaction of ethyl 3,4-bis(2-methoxy-ethoxy)benzoate with nitric acid in the presence of sulfuric acid to prepare ethyl 4,5-bis-(2-methoxyethoxy)-2-nitrobenzoate;
- causing a reaction of the ethyl 4,5-bis(2-methoxy-ethoxy)-2- nitrobenzoate with hydrogen in the presence of a metallic catalyst to prepare ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate;
- and causing a reaction of the ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate with an orthoformic ester in the presence of ammonium acetate to prepare 6,7-bis(2-methoxyethoxy)quinazolin-4-one.
A process for preparation of 6,7-bis(2-methoxyethoxy)-quinazolin-4-one, which comprises the steps in order of:
- causing a reaction of ethyl 3,4-dihydroxybenzoate with 2-chloroethyl methyl ether in an organic solvent in the presence of a base to prepare ethyl 3,4-bis(2-methoxyethoxy)benzoate;
- causing a reaction of the ethyl 3,4-bis(2-methoxyethoxy)benzoate with nitric acid in the presence of sulfuric acid to prepare ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate;
- causing a reaction of the ethyl 4,5-bis -(2-methoxyethoxy)-2-nitrobenzoate with hydrogen in the presence of a metallic catalyst to prepare ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate;
- and causing a reaction of the ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate with an orthoformic ester in the presence of ammonium acetate to prepare 6,7-bis(2-methoxyethoxy)quinazolin-4-one.
Dependencies are inferred from the claim text.