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CAS No. : | 1033771-61-7 | MDL No. : | MFCD26407201 |
Formula : | C16H15N3O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 345.31 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With caesium carbonate;palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 80℃; | Synthesis of [2-nitro-4-(3-nitrophenylamino)phenyl]acetic acid ethyl ester(4); [0096] To a flask are charged 3-nitroaniline (6.9 g, 50 mmol), (4-bromo-2- nitrophenyl)acetic acid ethyl ester (14.4 g, 50 mmol), xantaphos (868 mg, 1.5 mmol),Pd(OAc)2 (225 mg, 1 mmol), Cs2CO3 (23 g, 70 mmol) and 1,4-dioxane (100 mL). The mixture is heated at 110 0C overnight. It is cooled to room temperature and filtered through Celite. The filtrate is concentrated and purified by column chromatography(ISCO, gradient, 0-100% EtOAc/hexane) to give the desired product. LC-MS (m/z)346.1 (M++l). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With hydrogen; acetic acid at 20℃; | 1 Synthesis of 6-(3-aminophenylamino)-l,3-dihydroindol-2-one (5); [0098] To a solution of [2-nitro-4-(3-nitrophenylamino)phenyl]acetic acid ethyl ester (14.6 g, 0.042 mol) in acetic acid (250 mL) is added 10% Pd/C (10 wt%, 1.46 g).The mixture is stirred under a hydrogen balloon at room temperature overnight. The mixture is filtered through Celite. The filtrate is concentrated and purified (silica gel,EtOAc/hexane, gradient, 0-100%) to give the desired product. 1H NMR (400 MHz,DMSO-(I6) δ 10.18 (s, 1 H), 7.76 (s, 1 H), 6.98 (d, 1 H), 6.85 (t, 1 H), 6.58 (d, 1 H), 6.55(m, 1 H), 6.35 (m, 1 H), 6.25-6.20 (m, 1 H), 6.10-6.05 (m, 1 H), 4.91 (s, 2 H), 3.33 (s, 2H); LC-MS (m/z) 240.1 (M++l). |
51% | With palladium 10% on activated carbon; hydrogen In acetic acid at 20℃; |