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CAS No. : | 1068-90-2 | MDL No. : | MFCD00009146 |
Formula : | C9H15NO5 | Boiling Point : | - |
Linear Structure Formula : | CH3CONHCH(COOCH2CH3)2 | InChI Key : | ISOLMABRZPQKOV-UHFFFAOYSA-N |
M.W : | 217.22 | Pubchem ID : | 14041 |
Synonyms : |
Diethyl 2-acetamidomalonate
|
Chemical Name : | Diethyl 2-acetamidomalonate |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | 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 |
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Example 28 1 - [ (5-CHLORO-1, 2,3, 4-tetrahydroisoquinolin-3-yl) METHYL]-1-METHYL-1, 2- dihydrospiro [indole-3, 4'-piperidine] (A) 5-CHLORO-L-OXO-1, 2,3, 4-tetrahydroisoquinoline-3-carboxylic acid To a stirred suspension of 3-chloro-2-methylbenzoic acid (10.00 g, 58.6 mmol) in methanol (100 mL) was added dropwise thionyl chloride (8.5 mL, 117.2 mmol) at 0 C. The reaction mixture was refluxed for 2 h. After cooling down to room temperature, the reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate (300 ML), washed with 1N NaOH solution (100 mL), water (100 mL) and brine (100 ML), dried (NA2S04), filtered, and concentrated to give 10.86 g of methyl ester as colorless oil. A mixture of this ester (10.80 g, 58.5 mmol), N-bromosuccinimide (10.45 g, 64.4 mmol), and benzoyl peroxide (0.71 g, 2.9 mmol) in carbon tetrachloride (70 mL) was refluxed for 3 h. After cooling down to room temperature, the reaction mixture was filtered and the filtrate wad concentrated to give 16.30 g of <strong>[188187-03-3]methyl 3-chloro-2-bromomethylbenzoate</strong> as a colorless oil. To a stirred suspension of NaH (2.45 g, 61.3 mmol) in DMF (50 mL) was added dropwise a solution of diethyl acetamidomalonate (12.10 g, 55.7 mmol) in DMF (50 mL) at room temperature. After 15 min stirreing, a solution of methyl 3-chloro-2- bromomethylbenzoate (16.3 g, 58. 5 mmol) in DMF (50 mL) at room temperature. After 18 h stirring, the reaction mixture was concentrated. The residue was dissolved in ethyl acetate (800 ML), washed with water (200 mL x 2) and brine (200 mL), dried (NA2S04), filtered, and concentrated to give 21.5 g of yellow solid, which was purified by silica gel column chromatography (hexane/ethyl acetate: 2/1 to 111) to afford 14.33 g (64.3 %) of coupling product as a white solid. A mixture of this solid (13.90 g, 34.7 mmol) and 47 % HBr (160 mL) was refluxed for 24 h. After cooling down to room temperature, the solid formed was collected by filtration and dried togive 6.16 g (78.6 %) of title compound as a cream color solid. LHNMR (300MHZ, DMSO-D6) O8. 26 (1H, d, J = 4. 0 HZ), 7.85 (1H, dd, J = 1.1, 7.7 Hz), 7.64 (1H, dd, J = 1. 3, 8. 1 HZ), 7.39 (1H, dd, J = 7. 9,7. 9 HZ), 4.34-4. 28 (1H, m), 3.42-3. 36 (1H, overlapped with water peak at 3.36 ppm), 3.26 (1H, dd, J = 6.8, 16.9 Hz). |