Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1982-06-07
1984-08-07
Daus, Donald G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
C07D23732
Patent
active
044645325
ABSTRACT:
A novel process for producing 7-alkoxycarbonyl-6,8-dimethyl-4-hydroxymethyl-1-phthalazone, and its intermediates. 7-Alkoxycarbonyl-6,8-dimethyl-4-hydroxymethyl-1-phthalazone can be obtained by reacting substituted methylenetriphenylphosphorane with 3,5-dimethyl-4-alkoxycarbonylphthalic anhydride to obtain 6-alkoxycarbonyl-5,7-dimethyl-.DELTA..sup.3,.alpha. -substituted methylenephthalide, reacting the latter with hydrazine to obtain a phthalazone derivative, hydrolyzing the latter, halogenating the hydrolyzate to obtain 7-alkoxycarbonyl-6,8-dimethyl-4-(.alpha.-halogeno-.alpha.-substituted methyl)-1-phthalazone and then directly hydrolyzing and decarboxylating the latter or, when said 7-alkoxycarbonyl-6,8-dimethyl-4-(.alpha.-halogeno-.alpha.-substituted methyl)-1-phthalazone is 7-alkoxycarbonyl-6,8-dimethyl-1-phthalazone-4-.alpha.-halogenoacetic acid, reacting it with a carboxylic acid salt such as sodium acetate and simultaneously decarboxylating the acyloxylated compound and then hydrolyzing the decarboxylated product or firstly decarboxylating the 1-phthalazone-4-.alpha.-halogenoacetic acid derivative, reacting the decarboxylated product with said carboxylic acid salt and then hydrolyzing the reaction product or when said 7-alkoxycarbonyl-6,8-dimethyl-4-(.alpha.-halogeno-.alpha.-substituted methyl)-1-phthalazone is 7-alkoxycarbonyl-4-(.alpha.-carbamoyl-.alpha.-halogenomethyl-6,8-dimethyl- 1-phthalazone, reacting it with said carboxylic acid salt and then hydrolyzing and decarboxylating the acyloxylated compound simultaneously.
REFERENCES:
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Panomvana, D. L., "Prolonged Duration of Action of Dyphylline Through Prodrugs," Dissertation Abst. 40: #4232B.
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Nishizawa Rinzo
Takei Yukio
Yoshida Masao
Daus Donald G.
Hendricks G.
Nields Henry C.
Nippon Kayaku Kabushiki Kaisha
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