3,3-d1-substituted phthalides and intermediates and processes

Details 3,3-d1-substituted phthalides and intermediates and processes 3,3-d1-substituted phthalides and intermediates and processes

C - Chemistry, Metallurgy

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C07D 471/06 (2006.01) B41M 5/145 (2006.01) C07D 207/337 (2006.01) C07D 209/00 (2006.01) C07D 209/20 (2006.01) C07D 209/86 (2006.01) C07D 307/88 (2006.01) C07D 333/24 (2006.01) C07D 455/04 (2006.01)

Patent

CA 1088938

ABSTRACT OF THE DISCLOSURE Process comprises the combination of the three steps of condemsing 3-N(R)2-4-X-benzoic acid with an aromatic or hetero- cyclic aldehyde, YiCHO, under acidic conditions to produce 3-Y-5- X-6-N(R)2phthalide (II), condensing said phthalide with a compound of the formula Z-H under alkaline or acid conditions to produce 2-(.alpha.-Y-.alpha.-Z)methyl-4-X-5-N(R)2benzoic acid (III), and oxidizing said benzoic acid to produce 3-Y-3-Z-5-X-6-N(R)2phthalide (I) where: R is hydrogen, non-tertiary alkyl of one to four carbon atoms, benzyl or substituted benzyl; X is hydrogen or halo; Y is 4-R1-3-R2-2-R1-phenyl, 1-R5-2-R6-5/6-R4-3-indolyl, 9-R7-3- carbazolyl, 9-julolidinyl, 3,4-dioxymethylenephenyl, 2-thienyl, 1-R8-2-pyrrolyl, or 4-pyridinyl; and Z is 4-R1-3-R2-2-R1-phenyl, 1-R5-2-R6-5/6-R4-3-indolyl or 1-R8-2-pyrrolyl which are useful as colorless precursor color formers in carbonless duplicating and in thermal marking systems. The intermediates, 3-Y-5-X-6-N(R)2- phthalides (II) and 2-(.alpha.-Y-.alpha.-Z)methyl-4-X-5-N(R)2benzoic acids (III) also have utility as colorless precursor color formers in carbonless duplicating and thermal marking systems.

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