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US 6,310,222 B1Granted
Production method of 5-phthalancarbonitrile compound, intermediate therefor and production method of the intermediate
AssigneeSumika Fine Chemicals Co., Ltd.
InventorsTetsuya Ikemoto, Masami Igi
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Abstract
The present invention provides a production method of a 5-phthalancarbonitrile compound, which comprises the use of a novel compound of the formula [I] wherein X is chlorine atom, bromine atom or iodine atom, as a key intermediate; intermediate; and the process of preparing intermediates.
Claims7
A compound of the formula [III]
A compound of the formula [IV]
An oxime compound of the formula [V]
A method of producing a compound of the formula
- wherein Y is selected from the group consisting of CH2OH, CHO, and CH═NOH, and wherein (A) when Y is CH2OH, the method comprises
- (1) reacting a compound of the formula [II-b]
- wherein R1b is alkyl having 1 to 5 carbon atoms, tetrahydropyran-2-yl, alkoxymethyl wherein an alkoxyl moiety has 1 to 5 carbon atoms, 1-alkoxyethyl wherein an alkoxyl moiety has 1 to 10 carbon atoms, or trialkylsilyl wherein each alkyl moiety has 1 to 5 carbon atoms, and X is a chlorine atom, bromine atom or iodine atom, with magnesium or a lithium-containing compound to form a Grignard reagent or organolithium compound,
- (2) reacting the Grignard reagent or organolithium compound with p-fluorobenzaldehyde to form a coupling compound of the formula
- and
- (3) deprotecting R1b of the coupling compound formed in step (2) and cyclizing the coupling compound to form the compound of formula [III]
- and (B) when Y is CHO, the method comprises oxidizing a compound of the formula [III]
- with an oxidizing agent to form the compound of formula [IV]
- and (C) when Y is CH═NOH, the method comprises reacting a compound of the formula [IV]
- with hydroxylamine or a mineral acid salt thereof to form the compound of formula [V]
7 more elements
Dependencies are inferred from the claim text.