反応 #79690

反応方程式

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

ammonium hydroxide

HCl

→

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

収率 37.0%

溶媒

THF

ethyl acetate

反応条件

後処理

1. 1
   抽出The aqueous layer was extracted twice with ethyl acetate
2. 2
   洗浄The combined organic extracts were washed with saturated brine
3. 3
   乾燥dried over magnesium sulfate
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他The residue was purified by column chromatography on silica gel (elution with gradient methylene chloride/ethyl acetate)

実験手順

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.

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