Structure of 205877-13-0
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 205877-13-0 |
Formula : | C8H11NO2 |
M.W : | 153.18 |
SMILES Code : | OCC1=CC=CC(OC)=C1N |
MDL No. : | MFCD09029933 |
InChI Key : | NGKKHKCCXJPKGW-UHFFFAOYSA-N |
Pubchem ID : | 592703 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
100% | With borane-THF; In tetrahydrofuran; at 0 - 20℃; for 1.66667h;Inert atmosphere; | General procedure: To a solution of 6-chloroanthranilic acid (1.5 g, 8.74 mmol) in THF (5 mL) was added dropwise 1.08 M borane-tetrahydrofuran complex in THF (24.3 mL, 26.2 mmol) at 0 C under an Ar atmosphere for 10 min. After 1.5 h with stirring at 30 C, the solution was cooled at 0 C, added aqueous THF (THF/H2O = 1:1, 60 mL) and potassium carbonate, and extracted with diethyl ether three times. The combined organic extracts were washed with brine, dried over Na2SO4, and evaporated in vacuo. The residue was crystallized from AcOEt to give 1a (1.2 g, 88%) as a white needle crystal. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With manganese(IV) oxide; In dichloromethane; at 20℃; for 23h;Inert atmosphere; | General procedure: To a solution of 1a (1.2 g, 7.61 mmol) in CH2Cl2 (20 mL) was added MnO2 (2.6 g, 30.1 mmol) and stirred at rt under an Ar atmosphere. After 23 h with stirring, the reaction mixture was filtrated and evaporated. The residue was crystallized from AcOEt to give 7a (1.0 g, 85%) as a yellow needle crystal. |
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