반응 #640624

반응 방정식

Sodium tert-butoxide

1-acetyl-2-[(4-isopropyl-thiazol-2-yl)-carbonylamino]-3-methyl-4-methoxy-benzene

→

title compound

수율 108.3%

2-(4-isopropylthiazol-2-yl)-4-hydroxy-7-methoxy-8-methyl-quinoline

수율 108.3%

용매

ethyl acetate

tert-butanol

반응 조건

후처리

1. 1
   기타at ambient temperature
2. 2
   기타the reaction
3. 3
   workup.WAITThe reaction mixture was left
4. 4
   온도to cool to ambient temperature
5. 5
   세척The organic layer was washed with 1M aqueous potassium hydrogen sulphate (75 mL), water (50 mL), brine (50 mL)
6. 6
   건조dried over sodium sulphate
7. 7
   여과filtered
8. 8
   기타the solvent removed under vacuum

실험 절차

Sodium tert-butoxide (3.20 g, 28.6 mmol., 2.1 eq.) was added portion wise, at ambient temperature, to a solution of 1-acetyl-2-[(4-isopropyl-thiazol-2-yl)-carbonylamino]-3-methyl-4-methoxy-benzene (4.52 g, 13.6 mmol., 1.0 eq.) in dry tert-butanol (45 mL). The reaction mixture was stirred at 90° C. for 4 hours. LCMS analysis showed the reaction to be complete. The reaction mixture was left to cool to ambient temperature and then diluted with ethyl acetate (100 mL). The organic layer was washed with 1M aqueous potassium hydrogen sulphate (75 mL), water (50 mL), brine (50 mL), dried over sodium sulphate, filtered and the solvent removed under vacuum to give 4.63 g (99%) of the title compound as an off white solid. 1H NMR (500 MHz, CDCl3) δ ppm 9.59 (br. s, 1 H), 8.26 (d, J=9.16 Hz, 1 H), 7.10 (s, 1 H), 7.03 (d, J=9.16 Hz, 1 H), 6.77 (s, 1 H), 3.98 (s, 3 H), 3.20 (spt, J=6.87 Hz, 1 H), 2.43 (s, 3 H), 1.39 (d, J=7.02 Hz, 6 H). LC-MS: 95% (UV), tR 2.24 min, m/z [M+1]+ 315.15.

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