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CAS No. : | 89590-22-7 | MDL No. : | MFCD06795900 |
Formula : | C7H5NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MGQPBXGHGXFKJW-UHFFFAOYSA-N |
M.W : | 135.12 | Pubchem ID : | 13720697 |
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-H315-H319-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 |
---|---|---|
68% | With sulfuric acid; In ethanol; for 3h;Reflux; | To a stirred solution of <strong>[3163-15-3]2-aminoresorcinol</strong> (4.03 g, 32.26 mmol) and triethylorthoformate (6.17 mL, 37.1 mmol) in ethanol (10 mL), catalytic amount ofconcentrated sulfuric acid (0.09 mL, 1.6mmol) was added. Then the mixture washeated to reflux for 3 h. After cooling, the reaction mixture was diluted withethyl acetate (100 mL) and water (60 mL). The organic layer was separated andwashed with water (60 mL×2), and then dried over anhydrous magnesium sulfate. Thecrude product was purified by silica gel column chromatography(dichloromethane/methanol = 100:1) to afford compound 3 as an off-white solid (2.96g, 68%); mp 185-189 C; 1H NMR (400 MHz, Acetone-d6) delta (ppm) 9.07 (s, 1H), 8.30(s, 1H), 7.25 (t, J = 8.0 Hz, 1H), 7.14 (d, J = 8.0 Hz, 1H), 6.83 (d, J = 8.0 Hz, 1H);HRMS (ESI): m/z, Calcd. for C7H6O2N [M+H]+: 136.0393, Found 136.0394. |
62% | With sulfuric acid; | EXAMPLE 1D 4-Hydroxybenzoxazole A mixture of 2.1 g. <strong>[3163-15-3]2-aminoresorcinol</strong> (Pfaltz & Bauer, A28620), 3.7 g. triethylformate and 0.1 g. sulfuric acid was heated at 130 C. for 30 minutes. After cooling, the remaining solid was recrystallized from ethyl acetate, 1.4 g. (62% yield). |
62% | at 130℃; for 2h; | The solution of XL-1 (1 g, 8 mmol) in triethyl orthoformate (10 mL) was stirred at 130 C. for 2 hrs. Then the excess triethyl orthoformate was removed by evaporation. The residue was purified by column over silica gel (PE:EA=10/1) to afford XL-2 (0.68 g, yield 62%). |
With toluene-4-sulfonic acid; for 0.5h;Inert atmosphere; Reflux; | The compound obtained in Example 32-1 (400 mg, 3.20 mmol) triethyl orthoformate (3.2 ml, 19.2 mmol) in solution,para-tosylic acid monohydrate(30 mg, 0.16 mmol) was added dropwise. Under an argon atmosphere, followed by stirring for 30 minutes under reflux conditions, it was solidified after completion of the reaction concentrated to dryness. The residue was purified by silica gel column chromatography (hexane / ethyl acetate) to give the title compound (232 mg, 54%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
for 3.0h;Heating / reflux; | 2-Aminoresorcinol hydrochloride (2 g) and triethylchloroformate (4.5 ml) were heated to reflux under nitrogen for 3 h. After cooling to room temperature, the reaction mixture was poured into a mixture of water (70 ml) and ethanol (20 ml). The mixture was stirred vigorously for 30 minutes, then left to stand at room temperature overnight. The beige precipitate which formed was collected by filtration, and dried by azeotroping with toluene to give the title compound as a beige solid (1.2 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.8% | With potassium carbonate; In N,N-dimethyl-formamide; acetone; at 20℃; for 4h; | Following the preparation protocol of Section 5.1.2.1, thereaction mixture of <strong>[4487-56-3]2,4-dichloro-5-nitropyridine</strong> (1c) (269 mg,1.39 mmol), K2CO3 (384 mg, 2.78 mmol) and 4-hydroxyl benzo[d]oxazole (171 mg, 1.27 mmol) in acetone (18 mL) and DMF (2 mL)was stirred at room temperature for 4 h to give the title compound2w as a white solid (324 mg, 87.8percent); mp 195?196 C; 1H NMR(400 MHz, Acetone d6) d (ppm) 9.07 (s, 1H), 8.54 (s, 1H), 7.77 (d,J = 8.0 Hz, 1H), 7.63 (t, J = 8.0 Hz, 1H), 7.43 (d, J = 8.0 Hz, 1H), 7.07(s, 1H); 13C NMR (100 MHz, Acetone d6) d (ppm) 159.52, 156.42,154.98, 153.03, 148.02, 144.10, 127.68, 117.43, 113.52, 110.71;HRMS (ESI): m/z, Calcd. for C12H7O4N3Cl [M+H]+: 292.0120, Found292.0109 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.7% | With potassium carbonate; In N,N-dimethyl-formamide; acetone; at -40℃; for 6h; | Following the preparation protocol of Section5.1.2.1, the reaction mixture of <strong>[3177-20-6]methyl 2,4-dichloropyrimidine-5-carboxylate</strong> (8e) (228 mg, 1.10 mmol), K2CO3 (276 mg,2.0 mmol) and 4-hydroxyl benzo[d]oxazole (3) (135 mg, 1.0 mmol)in DMF (1 mL) and acetone (9 mL) was stirred at 40 C for 6 h togive compound 9g as a white solid (268 mg, 87.7percent); mp 131?133C; 1H NMR (400 MHz, DMSO d6) d (ppm) 9.13 (s, 1H), 8.76 (s, 1H),7.80 (d, J = 8.0 Hz, 1H), 7.56 (t, J = 8.0 Hz, 1H), 7.37 (d, J = 8.0 Hz,1H), 3.93 (s, 3H); HRMS (ESI): m/z, Calcd. for C13H9O4N3Cl[M+H]+: 306.0276, Found 306.0273 |