تفاعل #2286318

معادلة التفاعل

[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-acetonitrile

[3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-acetonitrile

ethyl acetate

→

acetic acid

المردود 13.0%

[3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-acetic acid

المردود 13.0%

المذيبات

hydrochloric acid

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated
2. 2
   درجة الحرارةto reflux for 24 h
3. 3
   غسيلwashed with a saturated aqueous sodium chloride solution (20 mL) and water (10 mL)
4. 4
   استخلاصextracted with ethyl acetate (50 mL)
5. 5
   تجفيفdried over magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated under vacuum
8. 8
   أخرىThe resulting oil was purified by HPLC (acetonitrile/water with 0.1% trifluoroacetic acid)
9. 9
   أخرىThe desired fractions were collected
10. 10
    تركيزconcentrated
11. 11
    أخرىfreeze dried
12. 12
    أخرىThe resulting solid was purified by flash chromatography
13. 13
    غسيلeluted with 10% methanol in methylene chloride
14. 14
    أخرىThe desired fractions were collected
15. 15
    تركيزconcentrated under vacuum
16. 16
    أخرىto afford a solid which
17. 17
    أخرىwas dried under high vacuum

الإجراء التجريبي

A mixture of [3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-acetonitrile (55) (assume 0.180 mmol) in concentrated hydrochloric acid (4 mL) was heated to reflux for 24 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (75 mL) and washed with a saturated aqueous sodium chloride solution (20 mL) and water (10 mL). The water layers were combined and extracted with ethyl acetate (50 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under vacuum. The resulting oil was purified by HPLC (acetonitrile/water with 0.1% trifluoroacetic acid). The desired fractions were collected, concentrated and freeze dried. The resulting solid was purified by flash chromatography using silica gel eluted with 10% methanol in methylene chloride. The desired fractions were collected and concentrated under vacuum to afford a solid which was dried under high vacuum to afford 3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-acetic acid (56) (8.6 mg, 13% for 2 steps) as a white solid; EI(+)-HRMS m/z calcd for C16H16Cl2N2O3 (M+H)+ 355.0611, found 355.0611. MW=355.2235, Exact Mass=354.0538

المصدر