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CAS No. : | 848092-84-2 | MDL No. : | MFCD20690673 |
Formula : | C9H11NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KVKBPICSIFDGGR-UHFFFAOYSA-N |
M.W : | 197.19 | Pubchem ID : | 23132473 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
85% | at 140℃; for 4 h; | A mixture of formamide (29 mL), ammonium formate (3.41 g, 54 mmol) and methyl 2-amino-4-hydroxy-5-methoxybenzoate (6.56 g, 36.0 mmol) was heated to 140C for 4 h. After cooling to r.t., water (75 mL) was added. Afterstirring for 1 h, the precipitated 7-hydroxy-6-methoxy-3,4-dihydroquinazolin-4-one was filtered off, washed with waterand dried (grey solid, 5.86 g, 30.5 mmol, 85 percent). LC/ESI-MS: m/ z = 193 [M +H]+; m/ z = 191 [M-H]-; Rt = 1.53 min. |
85% | at 140℃; for 4 h; | A mixture of formamide (29 mL), ammonium formate (3.41 g, 54 mmol) and methyl 2-amino-4-hydroxy-5-methoxybenzoate (6.56 g, 36.0 mmol) was heated to 140°C for 4 h. After cooling to r.t., water (75 mL) was added. After stirring for 1 h, the precipitated 7-hydroxy-6-methoxy-3,4-dihydroquinazolin-4-one was filtered off, washed with water and dried (grey solid, 5.86 g, 30.5 mmol, 85 percent). LC/ESI-MS: m/z = 193 [M +H]+; m/z = 191 [M-H]-; Rt = 1.53 min. |
85% | at 140℃; for 4 h; | Step 4. A mixture of formamide (29 mL), ammonium formate (3.41 g, 54 mmol) and methyl 2-amino-4-hydroxy-5-methoxybenzoate (6.56 g, 36.0 mmol) was heated to 140° C. for 4 h. After cooling to r.t., water (75 mL) was added. After stirring for 1 h, the precipitated 7-hydroxy-6-methoxy-3,4-dihydroquinazolin-4-one was filtered off, washed with water and dried (grey solid, 5.86 g, 30.5 mmol, 85percent). LC/ESI-MS: m/z=193 [M+H]+; m/z=191 [M-H]-; Rt=1.53 min. |
76% | at 140℃; for 4 h; | Step 4. A mixture of formamide (29 mL), ammonium formate (3.41 g, 54 mmol) and crude material of step 3 (36.0 mmol) was heated to 140° C. for 4 h. After cooling to r.t., water (75 mL) was added. After stirring for 1 h, the precipitated 7-hydroxy-6-methoxy-3,4-dihydroquinazolin-4-one or 6-hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one, respectively, was filtered off, washed with water and dried (76-85percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | at 150℃; for 5 h; | 4.1.6 7-Hydroxy-6-methoxyquinazolin-4(3H)-one (14) A mixture of formamide (25 mL), ammonium formate (3.59 g, 57 mmol) and 13 (6.5 g, 33 mmol) was heated at 150 °C for 5 h. The mixture was cooled to room temperature, and water (100 mL) was added in order to precipitate the quinazolinone 14. After stirring for 1 h, the resulting precipitate was filtered off, washed with water and dried to obtain intermediate 14 as a white solid. Yield: 86percent, mp: >250 °C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | at 140℃; for 4 h; | Step 4. A mixture of formamide (29 mL), ammonium formate (3.41 g, 54 mmol) and crude material of step 3 (36.0 mmol) was heated to 140° C. for 4 h. After cooling to r.t., water (75 mL) was added. After stirring for 1 h, the precipitated 7-hydroxy-6-methoxy-3,4-dihydroquinazolin-4-one or 6-hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one, respectively, was filtered off, washed with water and dried (76-85percent). |
76% | at 140℃; for 4 h; | Step 4. A mixture of formamide (29 mL), ammonium formate (3.41 g, 54 mmol) and crude material of step 3 (36.0 mmol) was heated to 140°C for 4 h. After cooling to r.t., water (75 mL) was added. After stirring for 1 h, the precipitated 7-hydroxy-6-methoxy-3,4-dihydroquinazolin-4-one or 6-hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one, respectively, was filtered off, washed with water and dried (76-85percent). |