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CAS No. : | 21606-04-2 | MDL No. : | MFCD00034781 |
Formula : | C9H7NO6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DJMQLZPEBHSABD-UHFFFAOYSA-N |
M.W : | 225.16 | Pubchem ID : | 4399477 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
86.7% | methyl 2-carboxy-3-nitrobenzoate [MNA] obtained in Reference Example 2 (164 kg) was dissolved in dimethylformamide [DMF] (242 kg), diphenylphosphoryl azide [DPPA] (204 kg) was added thereto at room temperature, and triethylamine (87 kg) was added dropwise while maintaining at 20 to 35 C. After stirring at 20 to 30 C for about 3 hours, t-butyl alcohol (930 kg) was added to the reaction solution.. The temperature was risen to 85 to 90 C over 3 to 5 hours, and the solution was stirred for 1 to 2 hours under reflux (85 to 90 C).. The reaction solution was cooled, concentrated, and the residue was dissolved in ethyl acetate (1400 L).. The solution was washed successively with a mixture of 15 % hydrochloric acid (160 L) and water (1890 L), water (660 L), 5 % aqueous sodium bicarbonate solution (1100 kg) and water (660 L), and the organic layer was concentrated under reduced pressure.. methanol (300 kg) was added thereto, and concentrated under reduced pressure.. A seed crystal (15 kg) and methanol (450 kg) were added to the residue, and the mixture was heated to 50 to 60 C to dissolve it.. After cooled to 5 C, crystals were separated, washed with cold methanol (100 L), and dried to give methyl 2-t-butoxycarbonylamino-3-nitrobenzoate [BAN] (187.0 kg, 86.7 %).. The mother liquor and the washing were concentrated under reduced pressure, and cooled.. The precipitated crystals were centrifuged, washed with cold methanol, and dried to give second crystal of BAN. 1H-NMR (200MHz, CDCl3) delta: 1.50(9H, s), 3,96(3H, s), 7.23(1H, t), 8.10(1H, dd), 8.17(1H, dd) IR(KBr) cm-1:3360, 1730, 1705, 1580, 1520, 1490, 1440, 1365, 1355, 1310, 1270, 1240, 1150, 870, 835, 770, 725, 705 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.5% | Step 1 To a solution of 2-methoxycarbonyl-6-nitrobenzoic acid (18.3 g, 81.3 mmol) in N,N-dimethylformamide (24.1 mL) was added dropwise diphenyl azidophosphonate (22.8 g, 83.0 mmol) at room temperature, and the dropping funnel was washed with N,N-dimethylformamide (1.8 mL). Then, triethylamine (9.75 g, 96.4 mmol) was added dropwise thereto at 22-31 C., and the dropping funnel was washed with N,N-dimethylformamide (1.6 ml). The reaction mixture was stirred at 28-23 C. for 5 hr under a nitrogen atmosphere. The reaction was monitored by HPLC. To the reaction mixture was added dropwise tert-butyl alcohol (104 g) at room temperature, and the reaction mixture was heated to about 85 C. over 5 hr, and stirred at 85-87 C. for 4 hr. The reaction was monitored by HPLC. The reaction mixture was concentrated under reduced pressure at 50 C. or lower, and ethyl acetate (156 mL) and 1.3% hydrochloric acid (229 ml) were added thereto. The organic layer was separated, and washed successively with water (74 mL), 5% aqueous sodium hydrogen carbonate solution (117 ml) and water (74 mL), and concentrated under reduced pressure at 40 C. or lower (solidification). The solid was dissolved in methanol (42.3 ml) at about 55 C. Methanol (63.5 mL) was added to the solution, and the solution was cooled from 50 C. to about 5 C. over 3 hr. During cooling, seed crystals were added thereto at 36 C., and the mixture was stirred at about 5 C. for 2 hr. The crystals were collected by filtration, washed with cold methanol (18 mL), and dried under reduced pressure at 50 C. or lower to give methyl 2-(tert-butoxycarbonylamino)-3-nitrobenzoate (compound 19a, 17.5 g, 72.5%) as pale-yellow crystals. melting point: 92-94 C. IR (KBr): 3368, 1735, 1608, 1540, 1508 cm-1 1H-NMR (CDCl3): delta=9.61 (br s, 1H), 8.16 (dd, J=8.1, 1.5 Hz, 1H), 8.10 (dd, J=8.1, 1.5 Hz, 1H), 7.23 (t, J=8.1 Hz, 1H), to 3.95 (s, 3H), 1.50 (s, 9H) MS: m/z=314 (MNH4+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
> 90% | at 20℃; for 2h;Acidic conditions; | (1) Put 30 g of 3-nitrophthalic acid into a 500 ml reaction flask and add 300 ml of methanol (1:10, optionally 1:5 to 1:20, preferably 1:10 to 1:15). Sulfuric acid 30g (1:0.5-1:2, preferably 1:1) was warmed at reflux.(2) TLC monitoring, when the formation of the double esterification product exceeds the reduction of the raw material, the refluxing reaction is ended; below 50 C., the methanol is concentrated under reduced pressure to almost no fraction.(3) Add 200ml of water, control the temperature below 25C, add potassium carbonate to neutralize the pH to 7-8, and add 100ml of ethyl acetate to extract.The extract is concentrated and crystallized to obtain <strong>[13365-26-9]dimethyl 3-nitrophthalate</strong>, the aqueous layer is acidified to pH 4-5, stirred at room temperature for 2 hours, and the product is filtered to obtain methyl 3-nitro-2-carboxybenzoate (AM1). , Content more than 98%, yield more than 90%,Drying standby. |
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