Quinophthalone compound
A compound, quinophthalone technology, applied in the field of new quinophthalone compounds, can solve problems such as undisclosed compounds, and achieve the effects of excellent tinting strength, excellent brightness and tinting power
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[0087] Hereinafter, although this invention is demonstrated based on an Example, this invention is not limited to these. It should be noted that, in Examples and Comparative Examples, unless otherwise specified, "parts" and "%" are based on mass.
Synthetic example 1
[0090] Put 55 g of concentrated sulfuric acid in the flask, and add 7.0 g of 6,6'-methylene obtained by the method described in the literature (Polymer, Vol. 39, No. 20 (1998), p4949) while stirring under ice cooling. Diquinaldine (23.5 mmol). While keeping below 10°C, 6.1 g of 60% nitric acid was added dropwise, and stirring was continued for 1 hour at 10°C to 20°C. The reaction liquid was poured into 150 ml of ice water, and the pH was adjusted to 3 with 20 wt % sodium hydroxide aqueous solution. The precipitated powder was recovered by filtration under reduced pressure, and washed with water until neutral. After the obtained solid was air-dried at 70° C., the crude product was washed and filtered with 100 ml of hot ethyl acetate, followed by 60 ml of hot toluene to remove impurities to obtain 6.52 g (16.8 mmol) of intermediate (A). (Yield: 72%)
[0091] 1 H-NMR (DMSO-d6) δppm: 2.70 (s, 6H), 4.42 (s, 2H), 7.58 (d, J = 8.8Hz, 2H), 7.63 (d, J = 8.8Hz, 2H), 8.09 ( d,J=8.8H...
Synthetic example 2
[0096] 5.30 g of reduced iron and 135 ml of acetic acid were placed in the flask, and heated to 50° C. while stirring. Next, 4.50 g (11.6 mmol) of the compound (A) obtained in the synthesis example 1 was added keeping 70 degreeC or less. After the addition, the stirring was continued at 60° C. for 1 hr, and then the reaction solution was cooled to below 35° C., poured into 500 ml of ice water, and adjusted to pH 9 with 20% NaOH water. The resulting precipitate was filtered on celite under reduced pressure. The solid matter was recovered, dried under blown air at 70°C, added to a mixed solvent of 100ml dimethyl sulfoxide (DMSO) and 100ml N,N-dimethylformamide (DMF), and stirred at 90°C for 1 hr. The mixture was filtered on celite under reduced pressure, and the resulting filtrate was added to 1 L of water with stirring. The generated precipitate was recovered by filtration under reduced pressure and washed with water to obtain 3.80 g (11.6 mmol) of an intermediate (B). (yiel...
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