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CAS No. : | 23602-63-3 | MDL No. : | MFCD00275687 |
Formula : | C8H7ClO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NSKZAOKQZDLHGO-UHFFFAOYSA-N |
M.W : | 170.59 | Pubchem ID : | 2774358 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
88% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20℃; for 48.0h; | To the solution of <strong>[23602-63-3]5-chloro-2-hydroxy-3-methylbenzaldehyde</strong> (22.6 g, 0.13 mol) in THF (200 ml) was added tert-butyl (triphenylphosphoranyl) acetate (50g, 0.13 mol) followed by adding DBU (0.3 ML). The reaction mixture was stirred at room temperature for 48 hours. The reaction mixture was concentrated under vacuum. To the concentrated residue was added 10% ethyl acetate in hexane (100 ML). Solid was formed in the solution and filtered out. The filtrated was concentrated and chromatographed on silica gel (10% ethyl acetate in hexane) to give 33.4 g (88%) white SOLID. 1H NMR (300 MHz, CDCl3) No. 1. 56 (s, 9H), 2.32 (s, 3H), 6.20 (s, 1H), 6.44 (d, 1H, J = 16. 11 Hz), 7.13 (m, 1H), 7.35 (m, 1H), 8.01 (d, 1H, J = 16.11). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With N,N,N,N,N,N-hexamethylphosphoric triamide; formaldehyd; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; toluene; at 4 - 20℃; for 52h;Heating / reflux; | To the solution of ETHYLMAGNESIUM bromide (400 mL, 1.0 M in THF) was added 4- CHLORO-2-METHYLPHENOL (57 g, 0.4 mol) in 75 mL toluene slowly at 4 C. To the above solution was added tetramethylethylenediamine (45g, 0.39 mol) followed by adding PARAFORMALDEHYDE (30 g) then HMPA (72.1g, 0.4 mol) at room temperature. The reaction mixture was REFLUXED 4 hours then stirred at room temperature for 48 hours. The reaction mixture was quenched with 50% HCI (450 ml). The aqueous solution was extracted with ethyl acetate (4X250ML). Combined organic solution was washed with brine, dried over MGS04 and concentrated under vacuum. Concentrated residue was chromatographed on silica gel (5% ethyl acetate in hexane) to give 40.8 g (60%) OIL. 1H NMR (400 MHz, CECI3) 8 2. 25 (s, 3H), 7.36 (m, 2H), 9.8 (s, 1 H), 11.16 (s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 47 6-[4-(5-Chloro-2-hydroxy-3-methyl-benzyl)-piperazin-1-yl]-3H-pyrimidin-4-one 6-[4-(5-Chloro-2-hydroxy-3-methyl-benzyl)-piperazin-1-yl]-3H-pyrimidin-4-one was prepared using Procedure B from 6-piperazin-1-yl-3H-pyrimidin-4-one (Intermediate 4) and <strong>[23602-63-3]5-chloro-2-hydroxy-3-methylbenzaldehyde</strong> (available from Alfa Aesar, Ward Hill, Mass., USA). 1H NMR (400 MHz, CDCl3) δ 2.19 (s, 3H), 2.58-2.63 (m, 4H), 3.48-3.67 (m, 6H), 5.40 (s, 1H), 6.80-6.81 (m, 1H), 7.03-7.04 (m, 1H), 7.85 (s, 1H), 10.60 (br s, 1H), 12.45 (br s, 1H). Mass spectrum (ES) MH+=335. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With tetra(n-butyl)ammonium hydroxide; sodium hydroxide; In water; at 20℃; for 3.0h; | Stepi : <strong>[23602-63-3]5-chloro-2-hydroxy-3-methylbenzaldehyde</strong> [23602-63-3] was suspended in 5ml of dichloromethane and 5 ml of water. 1.47 ml (4.4 mmol, 3 eq.) of sodium hydroxide 1 N and 1.52 g (2.94 mmol, 2 eq.) of tetrabutyl ammonium hydroxide 50%, then iodomethane (457 μl, 5 eq.) were added to the solution. The mixture was stirred 3h at room temperature. The reaction mixture was extracted 3 times with dichloromethane, the combined organic layers were washed with brine, dried with anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (dichloromethane) to give 100 mg (yield 93%) of 5-chloro-2-methoxy-3-methylbenzaldehyde |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With piperidine; In ethanol; for 8.0h;Reflux; | 6-Chloro-8-methyl-2-oxo-2H-chromene-3-carboxylic acid ethyl ester was synthesized from 2-Hydroxy-4-methoxy-benzaldehyde (0.0187 mol) and diethyl malonate (0.0188 mol) in the presence of 0.1 mL of piperidine as a catalyst and ethanol as solvent. The reaction mixturewas refluxed for 8 hr and the reaction was monitored by TLC using benzene:ethyl acetate(4:1) as an eluent. The reaction mixture was allowed to cool to room temperature, then the reaction mass was quenched in to ice cold water and the solid obtained was filtered to obtain compound in good yield (90%), m.p. 140C-142C (Scheme 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In methanol; at 45℃; for 4.0h; | General procedure: Homopiperonylamine (10 mmol, 1.652 g) in anhydrous methanol(10 mL) was added into the anhydrous methanol solution of salicylide(10 mmol, 1.221 g), and the mixture was reacted at 45 for 4 h. Theresulted yellow solution was slowly evaporated at room temperature forone week, and the yellow block crystals thus formed (yield: 80%). |
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