반응 #79690

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9-[(3-iodophenyl)methyl]-4-hydroxy-5-carbomethoxy carbazole

ammonium hydroxide

HCl

→

9-[(3-iodophenyl)methyl]-4-hydroxy-5-carbamoyl carbazole

수율 37.0%

용매

THF

ethyl acetate

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후처리

1. 1
   추출The aqueous layer was extracted twice with ethyl acetate
2. 2
   세척The combined organic extracts were washed with saturated brine
3. 3
   건조dried over magnesium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated
6. 6
   기타The residue was purified by column chromatography on silica gel (elution with gradient methylene chloride/ethyl acetate)

실험 절차

A solution of the 9-[(3-iodophenyl)methyl]-4-hydroxy-5-carbomethoxy carbazole (170 mg, 0.37 mM) in 10 mL THF and 30 mL concentrated aqueous ammonium hydroxide was stirred vigorously at room temperature for 120 hours. The mixture was diluted with ethyl acetate and acidified to pH 2 with 5 N HCl. The aqueous layer was extracted twice with ethyl acetate. The combined organic extracts were washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel (elution with gradient methylene chloride/ethyl acetate) to afford 61 mg (37%) of the 9-[(3-iodophenyl)methyl]-4-hydroxy-5-carbamoyl carbazole as a white solid. 1H NMR (DMSO-d6) δ10.5 (s, 1H), 8.8 (br s, 1H), 8.4 (br s, 1H), 7.8 (dd, 1H, J=1 and 8 Hz), 7.6-7.4 (m, 4H), 7.3 (t, 1H, J=8 Hz), 7.1-6.9 (m, 3H), 6.6 (d, 1H, J=8 Hz), and 5.7 (s, 2H). IR (CHCl3, cm−1) 3423, 3201 (br), 1630, 1600, 1579, 1564, 1445, 1330, 1261, and 775. MS (ES) m/e 441, 443.

출처