1-amino-4-hydroxy-2-[(6-hydroxyhexyl)oxy]anthraquinone synthesis

Yield:-

Reaction Conditions:

with 1-methyl-pyrrolidin-2-one;potassium carbonate;phenol at 120; for 12 h;

Steps:

3.A Step A: Preparation of (9)

A three neck 250 ml round bottom flask was charged with 25 g (0.079 moles) of 1- amino-2-bromo-4-hydroxy anthraquinone [(8),] 54.5 g (0.55 moles) of 1-methyl-2- pyrollidinone, 92 g (0.78 moles) 1,6-hexane-diol, 8.8 g (0.94 moles) phenol, and 12 g (0.086 moles) potassium carbonate. The batch was heated to [120 C] and held for 12 hours. TLC (in ethyl acetate) found no residual starting material. The reaction was cooled to [50 C] and 150 g methanol was added. The reaction was then cooled to room temperature and filtered with a Buchner funnel. 300 g methanol was added to the resulting solid and then stirred and filtered. The resulting solid product was dried in an oven at [100 C.] The yield was 19.8 g. [13C] NMR analysis shows the material was 94% pure of Dye-3 [(9).]

References:

WO2004/24830,2004,A1 Location in patent:Page 28