Реакция #81559

Уравнение реакции

Methyl 4-[(1,1-dimethyl-3-phenyl-1H-indene-5-carbonyl)amino]benzoate

NaOH

HCl

→

title compound

Выход 94.5%

4-[(1,1-Dimethyl-3-phenyl-1H-indene-5-carbonyl)amino]benzoic acid

Выход 94.5%

Растворители

methanol

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Концентрированиеconcentrated under reduced pressure
2. 2
   workup.ADDITIONAfter addition of 15 mL of water
3. 3
   Экстракцияthe mixture was extracted with ethyl acetate (15 mL×3)
4. 4
   ПромывкаThe combined extracts were washed with water (10 mL)
5. 5
   Сушкаdried over magnesium sulfate
6. 6
   Другоеevaporated
7. 7
   ДругоеThe residue was triturated in etherhexane

Методика

Methyl 4-[(1,1-dimethyl-3-phenyl-1H-indene-5-carbonyl)amino]benzoate (359 mg, 0.90 mmol) was stirred with 4.5 mL of 2N NaOH in 5 mL of methanol and 5 mL of tetrahydrofuran for 10 hours. The solution was acidified with 1N HCl and concentrated under reduced pressure. After addition of 15 mL of water, the mixture was extracted with ethyl acetate (15 mL×3). The combined extracts were washed with water (10 mL), dried over magnesium sulfate, and evaporated. The residue was triturated in etherhexane to give 326 mg (94% yield) of the title compound as solids; 1H-NMR (DMSO-d6) δ1.39 (s, 6H), 6.68 (s, 1H), 7.39-7.53 (m, 3H), 7.64-7.68 (m, 3H), 7.85-7.97 (m, 6H), 10.54 (s, 1H), 12.75 (bs, 1H); MS m/e 384 (MH+).

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