3-(substituted phenyl)phthalides

Details 3-(substituted phenyl)phthalides 3-(substituted phenyl)phthalides

1984-04-23

1986-06-17

Michl, Paul R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546 94, 546269, 549 60, C07D30514

Patent

active

045957681

ABSTRACT:
Process comprises the combination of the three steps of condensing 3-N(R).sub.2 -4-X-benzoic acid with an aromatic or heterocyclic aldehyde, Y-CHO, under acidic conditions to produce 3-Y-5-X-6-N(R).sub.2 phthalide (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).sub.2 benzoic acid (III), and oxidizing said benzoic acid to produce 3-Y-3-Z-5-X-6-N(R).sub.2 phthalide (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-R.sup.1 -3-R.sup.2 -2-R.sup.1 -phenyl, 1-R.sup.5 -2-R.sup.6 -5/6-R.sup.4 -3-indolyl, 9-R.sup.7 -3-carbazolyl, 9-julolidinyl, 3,4-dioxymethylenephenyl, 2-thienyl, 1-R.sup.8 -2-pyrrolyl, or 4-pyridinyl; and Z is 4-R.sup.1 -3-R.sup.2 -2-R.sup.1 -phenyl, 1-R.sup.5 -2-R.sup.6 -5/6-R.sup.4 -3-indolyl or 1-R.sup.8 -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).sub.2 phthalides (II) and 2-(.alpha.-Y-.alpha.-Z)methyl-4-X-5-N(R).sub.2 benzoic acids (III) also have utility as colorless precursor color formers in carbonless duplicating and thermal marking systems.

REFERENCES:
patent: 2742483 (1956-04-01), Crounse
patent: 3185709 (1965-05-01), Munro et al.
patent: 3491112 (1970-01-01), Lin
patent: 3829322 (1974-08-01), Ozutsumi et al.
patent: 4045458 (1977-08-01), Kondo et al.
Bulletin de l'Academie des Sciences de l'URSS Classe des Sciencies Chemie 81-8 (1940) (C.A. 35 2488.sup.4).
Journal American Chemical Society 82 5143-5147 (1960).
Journal of the Chemical Society 680-687 (1965).

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