反応 #87890

反応方程式

1-(3,4-dimethylphenyl)-3-methyl-4-(3-bromo-2-methoxyphenyl)hydrazono-5-pyrazolone

3-carboxyphenylboronic acid

potassium hydroxide

water

→

3′-{N′-[1-(3,4-dimethylphenyl)-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene]hydrazino}-2′-methoxybiphenyl-3-carboxylic acid

溶媒

ethanol

反応条件

後処理

1. 1
   温度to about reflux temperature
2. 2
   ろ過The hot mixture was filtered
3. 3
   その他to remove the catalyst
4. 4
   濃縮The clear filtrate was concentrated under vacuum
5. 5
   workup.ADDITIONTo the residue, water (100 mL) was added
6. 6
   workup.STIRRINGstirred for about 30 minutes at about room temperature
7. 7
   ろ過The slurry was filtered
8. 8
   その他to give a yellowish orange solid product, which
9. 9
   洗浄was washed with water (50 mL)
10. 10
    その他dried in an oven at about 55° C. to about 60° C. for about 12 hours

実験手順

A mixture of 1-(3,4-dimethylphenyl)-3-methyl-4-(3-bromo-2-methoxyphenyl)hydrazono-5-pyrazolone (5 g) prepared as in Example 2, and 3-carboxyphenylboronic acid (2.99 g), bis(triphenylphosphine)palladium(II)chloride [PdCl2(PPh3)2] (0.42 g), potassium hydroxide (1.74 g) in ethanol. (250 mL) and water (30 mL) was heated to about reflux temperature and stirred for about 24 hours. The hot mixture was filtered to remove the catalyst. The clear filtrate was concentrated under vacuum. To the residue, water (100 mL) was added; acidified to pH 3-5 using hydrochloric acid and stirred for about 30 minutes at about room temperature. The slurry was filtered to give a yellowish orange solid product, which was washed with water (50 mL) and dried in an oven at about 55° C. to about 60° C. for about 12 hours.

出典