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CAS No. : | 4031-84-9 | MDL No. : | MFCD00277666 |
Formula : | C12H16N2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 236.27 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H312-H315-H319-H332-H335 | Packing Group: | |
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 |
---|---|---|
99% | With palladium 10% on activated carbon; hydrogen In ethyl acetate for 12h; | |
97% | With hydrogen In methanol | 10.C Step C.10-4 10-5A solution of 10-4 (5.72 g, 21.5 mmol) in methanol was catalytically hydrogenated with Pd/C, then filtered and concentrated to dryness to afford the desired product 5-amino-2-morpholin-4-yl-benzoic acid methyl ester 10-5 (4.94 g, 97% yield); m/z = 237 (M+H)+. |
97% | With palladium 10% on activated carbon; hydrogen In ethanol for 48h; | Methyl 5-amino-2-morpholinobenzoate 5 To a solution of methyl2-morpholino-5-nitrobenzoate 4 (9.30 g, 0.035 mol) in EtOH(50 mL) was added Pd on carbon (10 wt %, 0.93 g) and the reactionstirred under an atmosphere of hydrogen for 48 h. The reactionmixture was then filtered through a plug of Celite and the solventremoved in vacuo to give the title product 5 (8.04 g, 97%) as a paleyellow solid. m.p.: 119-121 °C (Lit [18]. 121-122 °C). RF: 0.39 (1:1petroleum ether-ethyl acetate). δH (400 MHz; CDCl3; Me4Si) 2.93(4H, t, J 4.0 Hz, N(CH2CH2)2O), 3.59 (2H, br s, NH2), 3.82 (4H, t,J 4.0 Hz, N(CH2CH2)2O), 3.87 (3H, s, OCH3), 6.77 (1H, dd, J 2.0,8.0 Hz, H-4), 6.95 (1H, d, J 8.0 Hz, H-3), 7.04 (1H, d, J 2.0 Hz, H-6). δC (100 MHz; CDCl3) 52.0 (OCH3), 53.6 (N(CH2CH2)2O), 67.3(N(CH2CH2)2O),117.5 (C-6),119.4 (C-4), 121.1 (C-3),127.4 (C-1),141.4(C-5), 144.2 (C-2), 168.1 (C]O). IR: νmax(ATR)/cm-1; 3452, 3365(NH), 2960 (CH aromatic), 2842 (CH alkane), 1700 (C=O ester),1628, 1498 (C=C aromatic), 1445, 1324 (CH alkane), 1243, 1112(C-O ether), 935, 825 (CH aromatic). m/z (ESI): 259 (MNa, 10%),237 (MH, 50), 205 (100). HRMS (ESI) Found (MNa):259.1051C12H16N2NaO3 requires 259.1053. Found (MH):237.1235C12H17N2O3 requires 237.1234. The 1H NMR data wasconsistent literature values [18]. |
97% | With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 24h; | |
97% | With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 24h; | |
74.9% | With water; iron; ammonium chloride In tetrahydrofuran; ethanol at 100℃; for 2h; | 1.3 A suspension of methyl 2-morpholino-5-nitrobenzoate (16.6 g, 62.4 mmol) obtained as a crude product in Step 2, reduced iron (17.4 g, 0.3 mol) and ammonium chloride (16.6 g, 0.3 mol) in tetrahydrofuran (160 ml), ethanol (320 ml) and water (80 ml) was heated under reflux at 100°C for 2 hr. After allowing to cool to room temperature, the mixture was filtered through celite and washed with ethanol. The solvent of the filtrate was evaporated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:3) to give methyl 5-amino-2-morpholinobenzoate (11.0 g, yield 74.9%). |
With iron; ammonium chloride In tetrahydrofuran; methanol; water at 100℃; for 3h; | ||
With hydrogen In ethyl acetate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In 1,2-dichloro-ethane at 20℃; for 16h; | |
With dmap In 1,2-dichloro-ethane |