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CAS No. : | 39634-98-5 | MDL No. : | MFCD09809436 |
Formula : | C7H7ClN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 186.60 | 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 |
---|---|---|
acetic acid; In dimethyl sulfoxide; | EXAMPLE 6 3-Chloro-4-hydroxybenzoic Acid (4-Hydroxy-1-naphthylmethylene)hydrazide To a solution of 3-chloro-4-hydroxybenzoic acid hydrazide (200 mg, 1.1 mmol) in DMSO (2 ml) was added 4-hydroxynaphthaldehyde and a catalytic amount of glacial acetic acid (5 drops). The reaction was stirred overnight under nitrogen and diluted with ethyl acetate. The solution was washed with saturated sodium bicarbonate, water, brine, and dried over MgSO4. The organic volume was concentrated in vacuo to give the crude product. The product was purified by silica gel column chromatography using CH2Cl2/MeOH as the mobile phase. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoroacetic acid; | 3-Chloro-4-hydroxybenzoic Acid {2-Methoxy-4-[2-(2-phenylpiperidin-1-yl)ethoxy]benzylidene}hydrazide This compound was prepared analogously to the compound described in the previous example starting from resin bound 3-chloro-4-hydroxybenzoic acid hydrazide (resin-[building block 1]) (2 g, ~2 mmoles), 4-(2-bromoethoxy)-2-methoxybenzaldehyde ([building block 2]) (0.73 g, 1.5 equivs.), and <strong>[3466-80-6]2-phenylpiperidine</strong> ([building block 3]) (3.0 g, 10 equivs.). After cleavage with 50% trifluoroacetic acid, the residue (1.0 g) was purified by column chromatography on silica gel (28 g) eluding with a mixture of methanol and dichloromethane (1:13). This afforded 0.24 g of the title compound. 1H-NMR (400 MHz, DMSO-d6): deltaH=1.4 (2H, m), 1.65 (4H, m), 2.25 (2H, m), 2.75 (1H, m), 3.16 (1H, d), 3.25 (2H, d), 3.83 (3H, s), 4.0 (2H, m), 6.50 (1H, d), 6.54 (1H, s), 7.07 (1H, d), 7.23 (1H, t), 7.35 (4H, m), 7.73 (1H, d), 7.77 (1H, dd), 7.96 (1H, d), 8.65 (1H, s), 10.9 (1H, s), 11.6 (1H, s). |