58287-76-6|4-Formyl-N,N-dimethylbenzamide| Ambeed

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Quality Control of [ 58287-76-6 ] Purity: 95% SDS Specification

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Product Details of [ 58287-76-6 ]

CAS No. :	58287-76-6
Formula :	C₁₀H₁₁NO₂
M.W :	177.20
SMILES Code :	O=C(N(C)C)C1=CC=C(C=O)C=C1
MDL No. :	MFCD07186279
InChI Key :	RXRYFFTVFMQTKA-UHFFFAOYSA-N
Pubchem ID :	10559205

Safety of [ 58287-76-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 58287-76-6 ]

* 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 [ 58287-76-6 ]

[ 58287-76-6 ] Synthesis Path-Downstream 1~35

1
[ 141-82-2 ]
[ 58287-76-6 ]
[ 194928-67-1 ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 4053 - 4061.

2
[ 16173-52-7 ]
[ 124-40-3 ]
[ 58287-76-6 ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 4053 - 4061.

3
2-[4-(dimethylcarbamoyl)phenyl]acetic acid [ No CAS ]
[ 58287-76-6 ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 1965 - 1968.

4
[ 58287-76-6 ]
3-bromo-8-[2,6-dichloro-3-[N-[4-(dimethylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyloxy]-2-methylimidazo[1,2-a]pyridine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 4053 - 4061.

5
[ 619-66-9 ]
[ 58287-76-6 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1'-carbonyldiimidazole; In tetrahydrofuran; water;	EXAMPLE 6 p-Formyl-N,N-dimethylbenzamide benzylamidinohydrazone hydrochloride A mixture of 15.0 g. of 4-carboxybenzaldehyde, 17.0 g. of N,N'-carbonyldiimidazole and 150 ml. of tetrahydrofuran is allowed to stand at room temperature for one hour. Dimethylamine is passed thru the above solution for one hour and the reaction mixture is allowed to stand at room temperature for 18 hours, then is heated at reflux temperature for one hour. Water is added and the solvent is distilled off. The residue is extracted with methylenechloride. The organic layer is washed with dilute hydrochloric acid and water, dried over magnesium sulfate and concentrated to an oil. The oil is triturated with a little methylene chloride and the insoluble material is filtered off. The mother liquor is concentrated and 7.9 g. of p-formyl-N,N-dimethylbenzamide is obtained as an oil.

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 4053 - 4061.
[2]Patent: US4289769,1981,A .

Yield	Reaction Conditions	Operation in experiment
		PREPARATION 58 4-(N,N-Dimethylcarbamoyl)benzaldehyde was obtained by reacting 4-formylbenzoic acid with dimethylamine hydrochloride according to a similar manner to that of Preparation 47. mp: 60-67 C. NMR (CDCl3, delta): 2.97 (3H, s), 3.15 (3H, s), 7.59 (2H, d, J=7.5 Hz), 7.94 (2H, d, J=7.5 Hz), 10.3 (1H, s)

Yield	Reaction Conditions	Operation in experiment
51%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In methanol; N,N-dimethyl-formamide; at 0 - 20℃;	General procedure: I: To a solution of 4-formylbenzoic acid (1.0 mmol) in DMF (0.61 M) at 0 C was added DMAP (1.1 equiv) and EDCI (1.0 equiv). The reaction mixture was stirred at 0C for 45 minutes. At this time amine (1.0 equiv) was added and the mixture was warmed to room temperature and stirred overnight. The resulting mixture was concentrated in vacuo, partitioned between 1.0 M HC1 and EtOAc and extracted with EtOAc (2x). The combinedorganic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Purification was achieved via flash column chromatography on Si02 (Hexanes/EtOAc: 1 / 1) to afford the product.; 4-Formyl-N-methylbenzamide (161 6-52a). Compound 161 6-52a was prepared viaProcedure I from methanamine (3.3 mL, 2.0 M in MeOH, 6.7 mmol) to yield a white solid (0.14 g, 13 %).
		By following the procedures of Example 1A and substituting for 3-nitrobenzaldehyde with the following: ... 4-methoxycarbonylbenzaldehyde; 3-methoxycarbonyl-4-methyl-benzaldehyde; 4-carboxybenzaldehyde; 4-carbamoylbenzaldehyde; 4-N,N-dimethylcarbamoylbenzaldehyde; and 3,4-methylenedioxybenzaldehyde;
		By following the procedures of Example 10A and substituting 3-chlorobenzaldehyde with the following: ... 4-methoxycarbonylbenzaldehyde; 3-methoxycarbonyl-4-methyl-benzaldehyde; 4-carboxybenzaldehyde; 4-carbamoylbenzaldehyde; 4-N,N-dimethylcarbamoylbenzaldehyde; and 3,4-methylenedioxybenzaldehyde;

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 8 p-Formyl-N,N-dimethylbenzamide p-tolylamidinohydrazone hydrochloride As for Example 6 when p-tolylaminoguanidine dihydrochloride is reacted with p-formyl-N,N-dimethylbenzamide the product of the Example is obtained.

9
[ 934828-07-6 ]
[ 58287-76-6 ]
[ 1030830-31-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2580 - 2584.

10
[ 1207452-95-6 ]
[ 58287-76-6 ]
[ 105-37-3 ]
[ 1207454-99-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; at 20℃;	To a mixture of <strong>[58287-76-6]4-formyl-N,N-dimethylbenzamide</strong> (960 mg, 5.42 mmol), (E)-4-(4-(diethoxymethyl)benzylideneamino) isobenzofuran-1(3H)-one (1.84 g, 5.42 mmol) and sodium methoxide (499 mg, 21.7 mmol) was added to ethyl propionate (30 mL) and the mixture was stirred at room temperature overnight. Then the resulting mixture was evaporated under reduced pressure and extracted with EtOAc (100 mL×4) and concentrated. This gave the crude product (250 mg). LC-MS (ESI) m/z: 545 (M+1)+

References: [1]Patent: US2010/35883,2010,A1 .Location in patent: Page/Page column 85.

11
[ 59434-19-4 ]
[ 58287-76-6 ]
[ 1207454-74-7 ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium sulfate; In acetonitrile;Reflux;	4-Aminoisobenzofuran-1(3H)-one (2.10 g, 14.1 mmol), <strong>[58287-76-6]4-formyl-N,N-dimethylbenzamide</strong> (2.50 g, 14.1 mmol) and dry MgSO4 (9.84 g, 82 mmol) were added to acetonitrile (170 mL) and stirred under reflux overnight. The mixture was filtered, and the solvent was evaporated under reduced pressure and the residue was re-crystallized to obtain 3.5 g of title compound as a pale solid. 1H-NMR (400 MHz, CDCl3) delta (ppm): 3.01 (s, 3H), 3.15 (s, 3H), 5.43 (s, 2H), 7.38-7.40 (d, J=7.6 Hz, 1H), 7.55-7.61 (m, 3H), 7.80-7.82 (d, J=7.6 Hz, 1H), 7.96-7.98 (d, J=8 Hz, 2H), 8.58 (s, 1H); LC-MS (ESI) m/z: 308 (M+1)+.
	With magnesium sulfate; In acetonitrile;Reflux;	Example 10 IB(¾)-NN-dimethyl-4-((l-oxo- l,3-dihydroisobenzofuran-4ylimino)methyl)benzamide[00686] 4-Aminoisobenzofuran- 1 (3H)-one (2.10 g, 14.1 mmol), <strong>[58287-76-6]4-formyl-N,N-dimethylbenzamide</strong> (2.50 g, 14.1 mmol) and dry MgS04 (9.84 g, 82 mmol) were added to acetonitrile (170 mL) and stirred under reflux overnight. The mixture was filtered, and the solvent was evaporated under reduced pressure and the residue was re-crystallized to obtain 3.5 g of title compound as a pale solid. ^-NMR (400 MHz, CDCI3) delta (ppm): 3.01 (s, 3H), 3.15 (s, 3H), 5.43 (s, 2H), 7.38-7.40 (d, J= 7.6 Hz, 1H), 7.55-7.61 (m, 3H), 7.80- 7.82 (d, J= 7.6 Hz, 1H), 7.96-7.98 (d, J= 8 Hz, 2H),8.58 (s, 1H); LC-MS (ESI) m/z: 308 (M+l)+.

References: [1]Patent: US2010/35883,2010,A1 .Location in patent: Page/Page column 80.
[2]Patent: WO2011/130661,2011,A1 .Location in patent: Page/Page column 153.

12
[ 619-66-9 ]
[ 124-40-3 ]
[ 58287-76-6 ]

Yield	Reaction Conditions	Operation in experiment
53%		To a suspension of 4-formylbenzoic acid (4.00 g, 26.7 mmol) in dry DCM (8 mL) were added thionyl chloride (2.92 g, 40.0 mmol) and DMF (0.6 mL) dropwise at ambient temperature under nitrogen. The reaction mixture was refluxed for 2 h. After cooling, this mixture was added to 33% dimethylamine in water (10.5 mL, 72 mmol) dropwise over 15 min in an ice-water bath, and the reaction mixture stirred for 1 h at the same temperature. The solvent was evaporated in vacuums. The residue was purified by chromatography on silica gel to give the title compound (2.5 g, yield 53%) as a yellow solid. 1H-NMR (400 MHz, DMSO-d6) delta (ppm): 2.86 (s, 3H), 3.30 (s, 3H), 7.60 (d, J=7.6 Hz, 2H), 7.95 (d, J=7.6 Hz, 2H), 10.04 (s, 1H); LC-MS (ESI) m/z: 178 (M+1)+.

References: [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 12347 - 12351.
Angew. Chem.,2018,vol. 130,p. 12527 - 12531,5.
[2]Patent: US2010/35883,2010,A1 .Location in patent: Page/Page column 80.
[3]Journal of Medicinal Chemistry,2014,vol. 57,p. 2334 - 2356.

13
[ 64-17-5 ]
[ 1207454-48-5 ]
[ 58287-76-6 ]
[ 1207455-10-4 ]

Yield	Reaction Conditions	Operation in experiment
44%	With sodium; In Ethyl propionate; at 0 - 30℃;	Sodium (115 mg, 5 mmol) was added to EtOH (10 mL) to afford sodium ethoxide. (E)-4-(4-fluorobenzylideneamino)isobenzofuran-1(3H)-one (500 mg, 1.96 mmol) and <strong>[58287-76-6]4-formyl-N,N-dimethylbenzamide</strong> (382 mg, 2.16 mmol) were dissolved in ethyl propionate (10 mL), and the sodium ethoxide solution was added dropwise to the mixture at 0 C., then the mixture were heated to 30 C. for 1 h. To the reaction mixture was added water and EtOAc, the organic phase was separated, washed with water and brine. The organic phase was dried over anhydrous sodium sulfate and then concentrated to afford the crude product. The crude product was purified by flash chromatography (MeOH: DCM 1:25) to give the title compound (400 mg, yield 44%). LC-MS (ESI) m/z: 461(M+1)+

References: [1]Patent: US2010/35883,2010,A1 .Location in patent: Page/Page column 86-87.

14
[ 619-66-9 ]
[ 68-12-2 ]
[ 58287-76-6 ]

Yield	Reaction Conditions	Operation in experiment
53%		Example 101 A 4-Formyl-N,N-dimethylbenzamide[00685] To a suspension of 4-formylbenzoic acid (4.00 g, 26.7 mmol) in dry DCM (8 mL) were added thionyl chloride (2.92 g, 40.0 mmol) and DMF (0.6 mL) dropwise at ambient temperature under nitrogen. The reaction mixture was refluxed for 2 h. After cooling, this mixture was added to 33% dimethylamine in water (10.5 mL, 72 mmol) dropwise over 15 min in an ice-water bath, and the reaction mixture stirred for 1 h at the same temperature. The solvent was evaporated in vacuums. The residue was purified by chromatography on silica gel to give the title compound (2.5 g, yield 53%) as a yellow solid. ^-NMR (400 MHz, DMSO-i/6) 8(ppm): 2.86 (s, 3H), 3.30 (s, 3H), 7.60 (d, J= 7.6 Hz, 2H), 7.95 (d, J= 7.6 Hz, 2H), 10.04 (s, 1H); LC-MS (ESI) m/z: 178 (M+l)+.

References: [1]Patent: WO2011/130661,2011,A1 .Location in patent: Page/Page column 153.

15
[ 1207454-48-5 ]
[ 58287-76-6 ]
[ 141-52-6 ]
[ 105-37-3 ]
[ 1207455-10-4 ]

Yield	Reaction Conditions	Operation in experiment
44%	In ethanol; at 0 - 30℃; for 1h;	Example 1 16AEthyl 3-(4-(dimethylcarbamoyl)phenyl)-2-(4-fluorophenyl)-4-oxo- 1 ,2,3,4-tetrahydroquinoline-5- carboxylate[00731] Sodium (1 15mg, 5mmol) was added to EtOH (10 mL) to afford sodium ethoxide. (£)-4-(4- fluorobenzylideneamino)isobenzofuran- 1 (3H)-one (500mg, 1.96mmol) and 4-formyl-NrV- dimethylbenzamide (382 mg, 2.16 mmol) were dissolved in ethyl propionate (10 mL), and the sodium ethoxide solution was added dropwise to the mixture at 0 C, then the mixture were heated to 30 C for lh. To the reaction mixture was added water and EtOAc, the organic phase was separated, washed with water and brine. The organic phase was dried over anhydrous sodium sulfate and then concentrated to afford the crude product. The crude product was purified by flash chromatography (MeOH: DCM 1 :25) to give the title compound (400 mg, yield 44%). LC-MS (ESI) m/z: 461(M+1)+

References: [1]Patent: WO2011/130661,2011,A1 .Location in patent: Page/Page column 168.

16
[ 1207452-95-6 ]
[ 58287-76-6 ]
[ 124-41-4 ]
[ 105-37-3 ]
[ 1207454-99-6 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 20℃;	Example 1 12A[00719] Ethyl 2-(4-(diethoxymethyl)phenyl)-3-(4-(dimethylcarbamoyl)phenyl)-4-oxo- 1 ,2,3,4- tetrahydroquinoline-5-carboxylate[00720] To a mixture of <strong>[58287-76-6]4-formyl-N,N-dimethylbenzamide</strong> (960 mg, 5.42 mmol), (£)-4-(4-(diethoxymethyl)benzylideneamino) isobenzofuran-l(3H)-one (1.84 g, 5.42 mmol) and sodium methoxide (499 mg, 21.7 mmol) was added to ethyl propionate (30 mL) and the mixture was stirred at room temperature overnight. Then the resulting mixture was evaporated under reduced pressure and extracted with EtOAc (100 mL x 4) and concentrated. This gave the crude product (250 mg). LC-MS (ESI) m/z: 545 (M+l)+.

References: [1]Patent: WO2011/130661,2011,A1 .Location in patent: Page/Page column 164-165.

17
[ 58287-76-6 ]
[ 1207454-73-6 ]