Process for preparing substituted pyridone compounds

A process for preparing substituted pyridone compounds which comprises (a) admixing in the absence of a solvent (1) an amine of the formula R1—NH2 wherein R1 is an alkyl group having at least about 12 carbon atoms, an aryl group, an arylalkyl group, or an alkylaryl group, and (2) a first ester of the formula

• 138
• wherein R2 is a cyano group and R3 is an alkyl group;
• (b) heating the mixture containing the amine and the first ester to a temperature of at least about 80° C. for a period of at least about 10 minutes to form an intermediate compound of the formula
• 139
• (c) admixing the intermediate compound with (1) a base, (2) a second ester of the formula
• 140
• wherein R4 is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group and R5 is an alkyl group, and (3) a solvent, wherein the intermediate compound and the second ester are present in relative amounts of at least about 1.1 moles of second ester per every one mole of intermediate, wherein the intermediate compound and the base are present in relative amounts of at least about 1.1 moles of base per every one mole of intermediate, and (d) heating the mixture containing the intermediate compound, the second ester, and the base to a temperature of at least about 80° C. for a period of at least about 30 minutes to form a pyridone compound of the formula
• 141
• or a salt thereof.

A process for preparing diazopyridone compounds which comprises (a) admixing in the absence of a solvent (1) an amine of the formula R1—NH2 wherein R1 is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and (2) a first ester of the formula

• 142
• wherein R2 is an electron withdrawing group and R3 is an alkyl group;
• (b) heating the mixture containing the amine and the first ester to form an intermediate compound of the formula
• 143
• (c) admixing the intermediate compound with (1) a base and (2) a second ester of the formula
• 144
• wherein R4 is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group and R5 is an alkyl group, said second ester being present in a molar excess relative to the intermediate compound, said base being present in a molar excess relative to the intermediate compound, (d) heating the mixture containing the intermediate compound, the second ester, and the base to form a pyridone compound of the formula
• 145
• or a salt thereof;
• and (e) reacting the pyridone compound with a diazonium salt of the formula
• 146
• wherein R10 is (i) an alkylene group, (ii) an arylene group, (iii) an arylalkylene group, (iv) an alkylarylene group, (v) an alkyleneoxy group, (vi) an aryleneoxy group, (vii) an arylalkyleneoxy group, (viii) an alkylaryleneoxy group, (ix) a polyalkyleneoxy group, (x) a polyaryleneoxy group, (xi) a polyarylalkyleneoxy group, (xii) a polyalkylaryleneoxy group, (xiii) a heterocyclic group, (xiv) a silylene group, (xv) a siloxane group, (xvi) a polysilylene group, or (xvii) a polysiloxane group, X and X′ each, independently of the other, is (i) a direct bond, (ii) an oxygen atom, (iii) a sulfur atom, (iv) a group of the formula —NR40— wherein R40 is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, or (v) a group of the formula —CR50R60— wherein R50 and R60 each, independently of the other, is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, Z and Z′ each, independently of the other, is (i) a hydrogen atom, (ii) a halogen atom, (iii) a nitro group, (iv) an alkyl group, (v) an aryl group, (vi) an arylalkyl group, (vii) an alkylaryl group, (viii) a group of the formula
• 147
• wherein R70 is an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, an alkoxy group, an aryloxy group, an arylalkyloxy group, an alkylaryloxy group, a polyalkyleneoxy group, a polyaryleneoxy group, a polyarylalkyleneoxy group, a polyalkylaryleneoxy group, a heterocyclic group, a silyl group, a siloxane group, a polysilylene group, or a polysiloxane group, (ix) a sulfonyl group of the formula —SO2R80 wherein R80 is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, an alkoxy group, an aryloxy group, an arylalkyloxy group, an alkylaryloxy group, a polyalkyleneoxy group, a polyaryleneoxy group, a polyarylalkyleneoxy group, a polyalkylaryleneoxy group, a heterocyclic group, a silyl group, a siloxane group, a polysilylene group, or a polysiloxane group, or (x) a phosphoryl group of the formula —PO3R90 wherein R90 is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, an alkoxy group, an aryloxy group, an arylalkyloxy group, an alkylaryloxy group, a polyalkyleneoxy group, a polyaryleneoxy group, a polyarylalkyleneoxy group, a polyalkylaryleneoxy group, a heterocyclic group, a silyl group, a siloxane group, a polysilylene group, or a polysiloxane group, and A is an anion to form a diazopyridone colorant of the formula
• 148

A process for preparing diazopyridone compounds which comprises (a) admixing in the absence of a solvent (1) a diamine of the formula H2N—R1—NH2 wherein R1 is an alkylene group, an arylene group, an arylalkylene group, or an alkylarylene group, and (2) a first ester of the formula

• 149
• wherein R2 is an electron withdrawing group and R3 is an alkyl group;
• (b) heating the mixture containing the amine and the first ester to form an intermediate compound of the formula
• 150
• (c) admixing the intermediate compound with (1) a base and (2) a second ester of the formula
• 151
• wherein R4 is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group and R5 is an alkyl group, said second ester being present in a molar excess relative to the intermediate compound, said base being present in a molar excess relative to the intermediate compound, (d) heating the mixture containing the intermediate compound, the second ester, and the base to form a dipyridone compound of the formula
• 152
• or a salt thereof;
• and (e) reacting the dipyridone compound with a diazonium salt of the formula
• 153
• wherein R20 is (i) an alkyl group, (ii) an aryl group, (iii) an arylalkyl group, (iv) an alkylaryl group, (v) an alkoxy group, (vi) an aryloxy group, (vii) an arylalkyloxy group, (viii) an alkylaryloxy group, (ix) a polyalkyleneoxy group, (x) a polyaryleneoxy group, (xi) a polyarylalkyleneoxy group, (xii) a polyalkylaryleneoxy group, (xiii) a heterocyclic group, (xiv) a silyl group, (xv) a siloxane group, (xvi) a polysilylene group, or (xvii) a polysiloxane group, X is (i) a direct bond, (ii) an oxygen atom, (iii) a sulfur atom, (iv) a group of the formula —NR40— wherein R40 is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, or (v) a group of the formula —CR50R60— wherein R50 and R60 each, independently of the other, is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, Z is (i) a hydrogen atom, (ii) a halogen atom, (iii) a nitro group, (iv) an alkyl group, (v) an aryl group, (vi) an arylalkyl group, (vii) an alkylaryl group, (viii) a group of the formula
• 154
• wherein R70 is an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, an alkoxy group, an aryloxy group, an arylalkyloxy group, an alkylaryloxy group, a polyalkyleneoxy group, a polyaryleneoxy group, a polyarylalkyleneoxy group, a polyalkylaryleneoxy group, a heterocyclic group, a silyl group, a siloxane group, a polysilylene group, or a polysiloxane group, (ix) a sulfonyl group of the formula —SO2R80 wherein R80 is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, an alkoxy group, an aryloxy group, an arylalkyloxy group, an alkylaryloxy group, a polyalkyleneoxy group, a polyaryleneoxy group, a polyarylalkyleneoxy group, a polyalkylaryleneoxy group, a heterocyclic group, a silyl group, a siloxane group, a polysilylene group, or a polysiloxane group, or (x) a phosphoryl group of the formula —PO3R90 wherein R90 is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, an alkoxy group, an aryloxy group, an arylalkyloxy group, an alkylaryloxy group, a polyalkyleneoxy group, a polyaryleneoxy group, a polyarylalkyleneoxy group, a polyalkylaryleneoxy group, a heterocyclic group, a silyl group, a siloxane group, a polysilylene group, or a polysiloxane group, and A is an anion to form a diazopyridone colorant of the formula
• 155