41764-74-3|3,4-Dimethoxybenzohydrazide| Ambeed

Structure of Veratrohydrazide
CAS No.: 41764-74-3

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Quality Control of [ 41764-74-3 ] Purity: 98% SDS Specification

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Product Details of [ 41764-74-3 ]

CAS No. :	41764-74-3
Formula :	C₉H₁₂N₂O₃
M.W :	196.20
SMILES Code :	O=C(NN)C1=CC=C(OC)C(OC)=C1
MDL No. :	MFCD00017061
InChI Key :	LJMQIGMMUZLDOC-UHFFFAOYSA-N
Pubchem ID :	1530859

Safety of [ 41764-74-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P280-P305+P351+P338-P304+P340-P405-P501

Application In Synthesis of [ 41764-74-3 ]

* 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.

Downstream synthetic route of [ 41764-74-3 ]

[ 41764-74-3 ] Synthesis Path-Downstream 1~54

1
[ 2150-38-1 ]
[ 41764-74-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydrazine hydrate monohydrate; In ethanol; for 3h;Reflux;	A mixture of methyl 3,4-dimethoxybenzoate (20mmol) and hydrazine hydrate (30ml) were refluxed in ethanol for 3h. The reaction proceeding was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature, the solvent was reduced and n-hexane was added to the reaction mixture. The resulted precipitate was collected and washed with cold water to give us pure 3,4-dimethoxybenzohydrazide as the intermediate (yield: 88%).
61%	With hydrazine hydrate monohydrate; In ethanol; for 2h;Reflux;	To a solution of methyl 3,5-trimethoxybenzoate (3) (0.89 g, 4.54 mmol) in absolute ethanol (15 mL), 5.7 mL (117.8 mmol) of hydrazine hydrate 64 % was added. The reaction mixture was kept under reflux for 2 hours, when TLC indi-cated the end of the reaction. Then, the media was poured into ice and the resulting precipitate was filtered out afford-ing the 3,5-trimethoxybenzohydrazide (6) obtained as a white solid in 61% yield. 1H NMR and 13C NMR data were observed to be in agreement with previous reports [31].
	With hydrazine hydrate monohydrate; In methanol; for 8h;Reflux;	General procedure: To a solution of methyl ester of aromatic carboxylic acid 2 (0.1 mol) in methanol (30 mL), hydrazine hydrate (0.2 mol) was added drop wise with stirring. The resulting mixture was allowed to reflux for 8 h. After the completion of the reaction as monitored by TLC, the excess methanol was distilled off under reduced pressure. The resulting acid hydrazide 3 was washed with cold water, dried and recrystallized from ethanol.

	With pyridine; hydrazine hydrate monohydrate; In ethanol; for 10h;Reflux;	General procedure: To a mixture corresponding ester (9a-n, 5.0 mmol) and hydrazine monohydrate (15.0 mmol) in ethanol, catalytic amount of pyridine (0.5 mL) was added and refluxed for 10 h. The reaction was monitored by TLC. After the completion of the reaction, ethanol was evaporated from the mixture, water was added and extracted using ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated under vacuum to get the crude mass. Finally, the products 10a-n were purified using column chromatography. (Yield 80-85%).
	With hydrazine hydrate monohydrate; In ethanol; for 12h;Reflux;	General procedure: A mixture of ester 2a-d (10 mmol) and hydrazine monohydrate 80%(200 mmol) in ethanol (20 ml) was stirred vigorously for 12 h at reflux.After this time, the reaction mixture was kept in the freezer for 1 h. Thesolid formed was filtered and washed with cold ethanol. Compounds 3adwere obtained pure in 72-89% yield.

References: [1]European Journal of Medicinal Chemistry,1985,vol. 20,p. 257 - 266.
[2]Letters in drug design and discovery,2012,vol. 9,p. 276 - 281.
[3]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 2644 - 2651.
[4]Letters in drug design and discovery,2018,vol. 15,p. 778 - 786.
[5]ChemMedChem,2020.
[6]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4223 - 4227.
[7]Journal of the American Chemical Society,1948,vol. 70,p. 1901.
[8]Heterocycles,2004,vol. 62,p. 143 - 147.
[9]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1297 - 1303.
[10]ACS Medicinal Chemistry Letters,2010,vol. 1,p. 145 - 149.
[11]Journal of Agricultural and Food Chemistry,2012,vol. 60,p. 1036 - 1041.
[12]Bulletin of the Korean Chemical Society,2012,vol. 33,p. 2741 - 2747.
[13]Journal of Medicinal Chemistry,2012,vol. 55,p. 7525 - 7545.
[14]Medicinal Chemistry Research,2014,vol. 23,p. 1661 - 1671.
[15]Bioorganic Chemistry,2016,vol. 69,p. 48 - 63.
[16]Letters in drug design and discovery,2016,vol. 13,p. 968 - 981.
[17]Pharmaceutical Chemistry Journal,2018,vol. 51,p. 907 - 917.
[18]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2369 - 2374.
[19]Australian Journal of Chemistry,2012,vol. 65,p. 1413 - 1419,7.
[20]Bioorganic and Medicinal Chemistry,2021,vol. 32.
[21]Molecules,2021,vol. 26.
[22]Journal of Enzyme Inhibition and Medicinal Chemistry,2022,vol. 37,p. 1098 - 1119.

2
[ 41764-74-3 ]
[ 120-14-9 ]
[ 102017-12-9 ]

References: [1]Journal of the American Chemical Society,1948,vol. 70,p. 1901.
[2]European Journal of Medicinal Chemistry,2009,vol. 44,p. 1853 - 1863.
[3]RSC Advances,2013,vol. 3,p. 4237 - 4245.
[4]Research on Chemical Intermediates,2014,vol. 40,p. 947 - 960.

3
[ 41764-74-3 ]
[ 122-51-0 ]
[ 5378-22-3 ]

References: [1]Organic Letters,2018,vol. 20,p. 6027 - 6032.
[2]Bulletin de la Societe Chimique de France,1966,p. 376 - 381.

4
[ 542-85-8 ]
[ 41764-74-3 ]
[ 122772-02-5 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 83 - 86.
[2]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 3839 - 3849.
[3]European Journal of Medicinal Chemistry,2014,vol. 71,p. 185 - 198.

5
[ 3943-77-9 ]
[ 41764-74-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrazine hydrate; In ethanol; for 18h;Reflux;	A solution of ethyl 3,4-dimethoxybenzoate (868 mg, 4.13 mmol.) and hydrazine hydrate (64 wt%, 600 µL, 12.4 mmol) in EtOH (0.3 mL) was refluxed for 18 h while stirring. After cooling to rt the solvent was evaporated and the residue was dissolved in water (10 mL). The resulting solution was extracted with EtOAc (10 x 10 mL) and the combined organic extracts were dried over Na2SO4 and evaporated in order to obtain 3,4-dimethoxybenzohydrazide 24 as a colourless solid (770 mg, 3.92 mmol, 95%). Mp. 132.8-134.4 C; 3307, 2939, 2845, 1626, 1500, 1275, 1148, 1073, 957, 635; 1H NMR (300 MHz, DMSO-d6) d 9.62 (s, 1H, NHNH2), 7.44 (dd, J = 8.2, 1.2 Hz, 1H, H6), 7.42 (d, J = 2.0 Hz, 1H, H2), 6.99 (d, J = 8.2 Hz, 1H, H5), 4.42 (s, 2H, NHNH2), 3.79 (s, 6H, C3-OCH3, C4-OCH3) ppm; 13C NMR (76 MHz, DMSO-d6) d 165.5 (CO2NHNH2), 151.0 (C4) 148.1 (C3), 125.4 (C1), 120.0 (C6), 110.8 (C5), 110.1 (C2), 55.5 (C3-OCH3/C4-OCH3), 55.4 (C3-OCH3/C4-OCH3) ppm; MS (ESI+): m/z (%) = 197.4 (100) [M+H]+, 219.3 (22) [M+Na]+. The analytical data are in accordance with the literature. [16]
72.7%	With hydrazine hydrate; In ethanol;Reflux;	General procedure: A solution of the isolated esters 2a-e (10mmol) in ethanol (20mL), hydrazine hydrate (97%, 3mL) was added and heated under reflux for 5-8h. After cooling, the formed precipitate was filtered off, washed with water, dried, and crystallized from ethanol.
72.7%	With hydrazine hydrate; In ethanol;Reflux;	General procedure: Hydrazine hydrate (97%, 30 mmol, 1.5 mL) was added to a solutionof the isolated esters 2a-e (10 mmol) in ethanol (20 mL), and themixture was heated at reflux for 5-8 h. After cooling, the resultingprecipitate was filtered off, washed with water, dried, and crystallizedfrom ethanol.

References: [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 4778 - 4790.
[2]Patent: WO2020/183422,2020,A1 .Location in patent: Page/Page column 36.
[3]European Journal of Medicinal Chemistry,2018,vol. 151,p. 705 - 722.
[4]Bioorganic Chemistry,2019,vol. 84,p. 150 - 163.
[5]Journal of Medicinal Chemistry,1984,vol. 27,p. 1565 - 1570.
[6]Acta poloniae pharmaceutica,2008,vol. 65,p. 527 - 534.
[7]European Journal of Medicinal Chemistry,2009,vol. 44,p. 3798 - 3804.
[8]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2010,vol. 49,p. 526 - 531.
[9]Journal of Heterocyclic Chemistry,2010,vol. 47,p. 838 - 845.
[10]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 7836 - 7841.
[11]Medicinal Chemistry Research,2012,vol. 21,p. 382 - 394.
[12]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 3839 - 3849.
[13]Medicinal Chemistry Research,2014,vol. 23,p. 2080 - 2092.
[14]Bioorganic Chemistry,2016,vol. 65,p. 126 - 136.
[15]Chemical Biology and Drug Design,2017,vol. 90,p. 236 - 243.
[16]Bioorganic Chemistry,2019,vol. 89.
[17]Monatshefte fur Chemie,2019,vol. 150,p. 1809 - 1824.
[18]RSC Medicinal Chemistry,2020,vol. 11,p. 1178 - 1184.

6
[ 41764-74-3 ]
[ 103-72-0 ]
[ 91759-67-0 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; for 4h;Reflux;	General procedure: Equimolar quantities of the benzohydrazides 3a-e (0.1mol) and allyl/phenyl isothiocyanate (0.1mol) in 125mL of absolute ethanol were heated under reflux for 4h. The solvent was evaporated under vacuum. The resulting solid was filtered off, dried and used for the following step as a crude product. A mixture of the crude products (10mmol) and 100mL of 2N NaOH was heated under reflux for 3h. The reaction mixture was cooled and acidified to pH 2 with concentrated HCl. The solid that precipitated was filtered off, washed with water, and recrystallized from 95% ethanol [59].
	In dimethyl sulfoxide; at 25℃; for 1h;	General procedure: A solution of benzoylhydrazine (0.20 g, 1.5 mmol) and phenylisothiocyanate (0.20 g, 1.5 mmol) in DMSO (3 mL) was stirred atroom temperature for 1 h. Then, KHSO4 (1.19 g, 8.75 mmol) wasdirectly added to the stirred solution at the room temperature andreacted for another 6 h. After the completion of the reactionmonitored by TLC, the solution was diluted with 30 mL water, andthe resulting precipitate was separated by filtration or extractedwith EA, concentrated and dried. The residue was purified by columnchromatography on silica gel with petroleum ether/ethyl acetateto afford the target product

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 83 - 86.
[2]Journal of Medicinal Chemistry,1984,vol. 27,p. 1565 - 1570.
[3]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 3839 - 3849.
[4]European Journal of Medicinal Chemistry,2014,vol. 71,p. 185 - 198.
[5]European Journal of Medicinal Chemistry,2018,vol. 151,p. 705 - 722.
[6]Chemistry and biodiversity,2018,vol. 15.
[7]Tetrahedron,2021,vol. 96.

7
[ 41764-74-3 ]
[ 2284-20-0 ]
[ 122772-04-7 ]

References: [1]Bulletin of the Korean Chemical Society,2012,vol. 33,p. 2741 - 2747.
[2]Australian Journal of Chemistry,2012,vol. 65,p. 1413 - 1419,7.
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 83 - 86.

8
[ 41764-74-3 ]
[ 57-06-7 ]
[ 108903-26-0 ]