Structure of 5785-06-8
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CAS No. : | 5785-06-8 |
Formula : | C8H10N2O2 |
M.W : | 166.18 |
SMILES Code : | O=C(NN)C1=CC=CC(OC)=C1 |
MDL No. : | MFCD00007601 |
Boiling Point : | No data available |
InChI Key : | VMZSDAQEWPNOIB-UHFFFAOYSA-N |
Pubchem ID : | 79848 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 |
* 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 |
---|---|---|
In ethanol; at 80℃; for 3h; | General procedure: 8-Methoxyquinoline-2-carbaldehyde (25, 0.534 mmol) was refluxedwith various substituted acylhydrazines (0.587 mmol, 1.1 eq) in ethanol(5-10 mL) to get acyl hydrazides of 8-hydroxyquinoline. After completionof reaction, quinoline acyl hydrazides were found as precipitateson cooling to -15 C. Precipitates were washed with coldethanol and dried under vacuum. These acyl hydrazides were used directlyfor one pot synthesis of 2,5-disubstituted-1,3,4-oxadiazole usingiodine/K2CO3 catalysed oxidative cyclization. To the acyl hydrazides(1.0 eq) in DMSO (5-10 mL), K2CO3 (3.0 eq) and iodine (1.2 eq) wereadded in sequence and refluxed at 110 C. After the completion, thereaction mixture was cooled and saturated solution of sodium thiosulfatewas added. The precipitates were collected and dried under highvacuum to get the respective compounds (33-50). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In methanol; for 2h;Reflux; | This aroylhydrazone was prepared by adapting a previous reportedprocedure [37]. 3,5-Diiodosalicylaldehyde (0.37 g, 0.99 mmol) wasdissolved in 10 mL methanol and a 10 mL methanolic solution of 3-methoxybenzhydrazide (0.17 g, 1.02 mmol) was added and the mixturewas refluxed with stirring for 2 h at room temperature. The resultingyellow colored crystalline precipitate formed was separated, filteredand recrystallized from DMF solution. The solution was allowed toevaporate slowly. After 2-3 d, small needle shaped crystals suitable forX-ray analysis was isolated and dried over P4O10 in vacuo.Analytical data for C15H12I2N2O3 (H2SMB): Yield: 0.47 g (89%;color: Yellow colored crystals; M.W.: 522.07 g mol-1; elemental analysiscalculated/found (%): C 34.51/34.22, H 2.32/2.18, N 5.37/5.26;1H NMR (400 MHz, DMSO-d6): δ 3.84 (3H, s, -OCH3), 7.2-7.54 (4H, m,aromatic), 7.87 (1H, d, aromatic), 8.06 (1H, d, aromatic), 8.44 (1H, s,]CH), 12.49 (1H, br, OH), 12.91 (1H, br, NH); FT-IR: ν (cm-1) 3247ν(OeH), 3190 ν(NeH), 1658 ν(C]O), 1604, ν(C]N); MS (ESI) m/z[M + H]+ 522.95, calculated m/z 522.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With acetic acid; In methanol; for 4h;Reflux; | The aroylhydrazone was synthesized by adapting a previouslyreported procedure [15]. Methanolic solutions of 3-methoxybenzhydrazide (0.166 g, 1 mmol) and 30,50-dichloro-20-hydroxyacetophenone (0.205 g, 1 mmol) were mixed and refluxedafter adding six drops of glacial acetic acid for 4 h. Single crystalssuitable for X-ray analysis obtained on evaporation of the resultingreaction mixture were separated, washed and dried over P4O10 invacuo (Scheme 1).Analytical data for C16H16Cl2N2O4 (H2CABH2O) Yield: 0.285 g(77%); color: yellow; M.W.: 371.21 g mol1; elemental analysiscalculated/found (%): C 51.77/51.87, H 4.34/4.55, N 7.55/7.61; 1HNMR (400 MHz, DMSO-d6): d 2.86 (3H, s, eCH3), 3.85 (3H, s,eOCH3), 7.22 (1H, q, aromatic), 7.5 (3H, m, aromatic), 7.63 (1H, d,aromatic), 7.68 (1H, d, aromatic), 11.55 (1H, br, OH), 14.43 (1H, br,NH); FTeIR: n (cm1) 3548 n(OeH), 3439 n(NeH), 1660 n(C]O),1592, n(C]N); MS (ESI) m/z (M1) 353.1, calculated m/z 352.04. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | General procedure: For 10 mL methanolic solution of 3-methoxybenzhydrazide (0.17 g, 1.00 mmol), 10 mL methanolic solution of 3′,5′-dichloro-2′-hydroxyacetophenone (0.21 g, 1.00 mmol) is added and refluxed for 3 h. Bis(acetylacetonato)dioxomolybdenum(VI) (0.33 g, 1.00 mmol) dissolved in10 mL methanol was added slowly to the above refluxing solution, and refluxation was continued for another 30 min. For the refluxing solution, 0.5 mL of respective heterocyclic base (pyridine for complex 2 and 3-picoline for complex 3 and 4-picoline for complex 4) was added and refluxed again for 21/2 h. Single crystals suitable for X-ray analysis obtained on slow evaporation of the resulting orange colored solutions were filtered off and washed with methanol and dried over P4O10 in vacuo (Scheme 1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | In methanol; for 4h;Reflux; | 3-Methoxybenzhydrazide (0.17 g, 1.00 mmol) dissolved in 10 mL methanol, 3′,5′-dichloro-2′-hydroxyacetophenone (0.21 g, 1.00 mmol) dissolved in 10 mL methanol was added and refluxed for 4 h. Single crystals suitable for X-ray analysis obtained on evaporation of the resulting reaction mixture were separated, washed and dried over P4O10 in vacuo [27]. Analytical data for C16H16Cl2N2O4 (H2CAB·H2O) Yield: 0.29 g (77%); color: Yellow; M.W.: 371.21 g mol-1; elemental analysis calculated/found (%): C 51.8/51.7, H 4.3/4.5,N 7.6/7.8; 1H NMR (400 MHz, DMSO-d6): δ 2.86 (3H, s,-CH3), 3.85 (3H, s, -OCH3), 7.22 (1H, q, aromatic), 7.5 (3H, m, aromatic), 7.63 (1H, d, aromatic), 7.68 (1H, d, aromatic), 11.55 (1H, br, OH), 14.43 (1H, br, NH); FT-IR: ν (cm-1) 3548 ν(O-H), 3439 ν(N-H), 1660 ν(C=O), 1592, ν(C=N). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | General procedure: For 10 mL methanolic solution of 3-methoxybenzhydrazide (0.17 g, 1.00 mmol), 10 mL methanolic solution of 3′,5′-dichloro-2′-hydroxyacetophenone (0.21 g, 1.00 mmol) is added and refluxed for 3 h. Bis(acetylacetonato)dioxomolybdenum(VI) (0.33 g, 1.00 mmol) dissolved in10 mL methanol was added slowly to the above refluxing solution, and refluxation was continued for another 30 min. For the refluxing solution, 0.5 mL of respective heterocyclic base (pyridine for complex 2 and 3-picoline for complex 3 and 4-picoline for complex 4) was added and refluxed again for 21/2 h. Single crystals suitable for X-ray analysis obtained on slow evaporation of the resulting orange colored solutions were filtered off and washed with methanol and dried over P4O10 in vacuo (Scheme 1). Analytical data for C21H17Cl2MoN3O5 ([MoO2(CAB)(py)] (1)): Yield: 0.34 g (61%); color: orange; M.W.:558.22 g mol-1; elemental analysis calculated/found (%): C45.2/45.3, H 3.1/3.1, N 7.5/7.5; 1H NMR (400 MHz, DMSO-d6):δ 2.96 (3H, s, -CH3), 3.89 (3H, s, -OCH3), 7.23-8.64(11H, aromatic); FT-IR: ν (cm-1) 1583 and 1545 ν(C=N), 1337 ν(C-O), 935 and 921 ν(Mo=O). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | General procedure: For 10 mL methanolic solution of 3-methoxybenzhydrazide (0.17 g, 1.00 mmol), 10 mL methanolic solution of 3′,5′-dichloro-2′-hydroxyacetophenone (0.21 g, 1.00 mmol) is added and refluxed for 3 h. Bis(acetylacetonato)dioxomolybdenum(VI) (0.33 g, 1.00 mmol) dissolved in10 mL methanol was added slowly to the above refluxing solution, and refluxation was continued for another 30 min. For the refluxing solution, 0.5 mL of respective heterocyclic base (pyridine for complex 2 and 3-picoline for complex 3 and 4-picoline for complex 4) was added and refluxed again for 21/2 h. Single crystals suitable for X-ray analysis obtained on slow evaporation of the resulting orange colored solutions were filtered off and washed with methanol and dried over P4O10 in vacuo (Scheme 1 |
A459164 [850350-02-6]
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