تفاعل #79690

معادلة التفاعل

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

ammonium hydroxide

HCl

→

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

المردود 37.0%

المذيبات

THF

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe aqueous layer was extracted twice with ethyl acetate
2. 2
   غسيلThe combined organic extracts were washed with saturated brine
3. 3
   تجفيفdried over magnesium sulfate
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated
6. 6
   أخرىThe residue was purified by column chromatography on silica gel (elution with gradient methylene chloride/ethyl acetate)

الإجراء التجريبي

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.

المصدر