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CAS No. : | 57998-96-6 | MDL No. : | MFCD00666132 |
Formula : | C12H12N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 216.24 | 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 |
---|---|---|
95% | With barium dihydroxide In water at 125℃; for 24h; | |
With barium dihydroxide In water | ||
With barium dihydroxide at 165℃; |
With barium hydroxide octahydrate In water at 150℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water | 1 EXAMPLE 1 EXAMPLE 1 A mixture consisting of 12.5 g. (0.058 mole) of 3',4'-dihydro-spiro-[imidazolidine-4,1'(2'H)naphthalene]-2,5-dione [Chemical Abstracts, Vol. 35, p. 65767 (1941)] and 54.6 g of barium hydroxide hexahydrate in 75 ml of water was refluxed for a period of 24 hours and then cooled to room temperature (~25° C.). The pH of the resulting solution was then adjusted to pH 7.0 with the aid of concentrated sulfuric acid and thereafter filtered. The filtrate was then readjusted to pH 5.0 and freeze-dried to give 6.0 g. of crude 1-amino-1,2,3,4-tetrahydro-1-naphthoic acid (m.p. 247°-248° C.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Stage #1: ammonium carbonate; 3,4-dihydronaphthalene-1(2H)-one With sodium cyanide; ammonia In ethanol; water at 125℃; for 3.5h; Autoclave; Stage #2: With hydrogenchloride In ethanol; water Autoclave; | 3. 2. Synthesis of 3’,4’-Dihydro-2H,2’H,5Hspiro[imidazolidine-4,1’-naphthalene]-2,5-dione (2, Scheme 1) (a modificationof the method reported by Sarges et al.1) A suspension of 13.3 mL (14.62 g, 100 mmol) of 3,4-dihydronaphthalen-1(2H)-one (1, Scheme 1), 7.35 g (150 mmol) NaCN, 28.8 g (300 mmol) (NH4)2CO3, 150 mL 96% C2H5OH and 160 mL 25% aqueous NH3 were heated in an autoclave at 125 °C for 3.5 h. After cooling to the room temperature, the reaction mixture was poured into 750 mLof water and acidified to pH 2 with 6 N HCl. The light brown product crystallized was filtered off and washed with water until the washings attained a neutral pH. The obtained product 2 was recrystallized from tetrahydrofuran. Yield: 18.5 g (86%); M. p. 243-244 °C (lit.1 240-242°C); Rf = 0.65; Anal. calcd. for C12H12N2O2: C, 66.65; H,5.59; N, 12.96; found: C, 66.28; H, 5.51; N, 12.96%; IR(KBr, cm-1): 3220 (N-H), 3051 (N-H), 2944 (arom.),2869 (CH2), 1767 (C=O), 1708 (C=O); 1H NMR (δ, DMSO-d6, ppm): 1.79-2.50 (m, 6H, aliph.), 7.05-7.24 (m, 4H,arom.), 8.54 (s, 1H, NH), 10.84 (s, 1H, NH); 13C NMR (δ,DMSO-d6, ppm): 18.5 (CH2), 28.6 (CH2), 33.6 (CH2), 63.2(spiro C-atom), 126.6 (CH, arom.), 126.7 (CH, arom.),128.1 (CH, arom.), 129.4 (CH, arom.), 134.4 (C, arom.),137.9 (C, arom.), 156.6 (C=O), 178.1 (C=O); 13C DEPT-135 (δ, DMSO-d6, ppm): 18.9 (CH2), 28.9 (CH2), 33.9(CH2), 127.0 (CH, arom.), 127.1 (CH, arom.), 128.5 (CH,arom.), 129.8 (CH, arom.). MS (m/z) 216 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With dmap; triethylamine; In dichloromethane; at 25℃; for 15h; | General procedure: Arylsulfonyl chloride (5.8mmol) was added drop-wise to a well stirred mixture of 1 (4.8mmol), triethylamine (4.8mmol) and catalytic amounts of DMAP in 10mL DCM, and stirred for 15h. The reaction mixture was neutralized with 1N HCl and extracted with dichloromethane (4×25mL). After evaporation of DCM, the crude product was recrystallized from ethanol-water solvent pair in order to obtain a white to pale yellow crystalline powder of the respective product. |