54-60-4|2-((4-Fluorophenyl)amino)benzoic acid| Ambeed

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Quality Control of [ 54-60-4 ] Purity: 95% SDS Specification

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Product Details of [ 54-60-4 ]

CAS No. :	54-60-4
Formula :	C₁₃H₁₀FNO₂
M.W :	231.22
SMILES Code :	O=C(O)C1=CC=CC=C1NC2=CC=C(F)C=C2
MDL No. :	MFCD01675229
Boiling Point :	No data available
InChI Key :	YQDLBCADRCGKQK-UHFFFAOYSA-N
Pubchem ID :	120159

Safety of [ 54-60-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 54-60-4 ]

* 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 [ 54-60-4 ]

[ 54-60-4 ] Synthesis Path-Downstream 1~35

1
[ 54-60-4 ]
[ 318-31-0 ]

Yield	Reaction Conditions	Operation in experiment
383 mg (59%)	With trichlorophosphate; In water;	13.2 2-Fluoroacridone N-(4-Fluorophenyl)anthranilic acid (0.70 gm; 3 mmol) and phosphorous oxychloride (3 ml) were stirred together and heated to 115 C. for 3.5 hours, then allowed to cool. The reaction mixture was placed on ice and small pieces of ice added, a vigorous reaction occurred with the evolution of hydrogen chloride. When the reaction had subsided, water (15 ml) was added and the mixture was boiled for 2 hours. On cooling, a solid precipitated out. This was filtered off and washed with water until the filtrate was colourless. The precipitate was further washed with cold methanol then diethyl ether and dried under vacuum to give 383 mg (59%) of 2-fluoroacridone.

References: [1]Archiv der Pharmazie,2009,vol. 342,p. 640 - 650.
[2]Bulletin de la Societe Chimique de France,1951,p. 318,322.
[3]Patent: US2004/191792,2004,A1 .
[4]Advanced Synthesis and Catalysis,2012,vol. 354,p. 701 - 711.
[5]Chemical Biology and Drug Design,2017,vol. 90,p. 926 - 935.

2
[ 54-60-4 ]
[ 2377-17-5 ]

Yield	Reaction Conditions	Operation in experiment
54%	With trichlorophosphate; at 130℃; for 2.0h;Inert atmosphere;	The mixture of compound 9a (100 mg, 0.43 mmol) and POCl3 (1 mL) was heated to 130 C under N2 for 2h. After evaporation of POCl3 under reduced pressure, the residue was poured into ice, basified with 37% NH4OH(aq) to pH 8, and extracted with EtOAc (10 mL × 3). The combined organic layer was dried over Na2SO4, filtered and the solvent removed in vacuo. The residue was purified by silica gel chromatography (MeOH: CH2Cl2 = 2:98 - 3: 97) to give 10a (54mg, 54%) as a solid. Mp 134-136 C . IR (KBr) 3059, 3034, 1637, 1523, 1478, 1437, 1177 cm-1. 1H NMR (300 MHz, DMSO-d6) δ 8.37 (dd, J = 0.9, 8.6 Hz, 1H), 8.30 (dd, J = 5.6, 9.2 Hz, 1H), 8.21 (dd, J = 0.9, 8.6 Hz, 1H), 8.04 (dd, J = 2.9, 10.1 Hz, 1H), 7.91 (m, 2H), 7.82 (m, 1H). ESI-MS m/z: 232.0 (M+H)+.
	With trichlorophosphate; at 80 - 150℃; for 2.25h;	General procedure: A mixture of 2-(phenylamino) benzoic acid (0.024 mol) andphosphorus oxychloride (5 mL) was heated on a water bath for15-20 min. at 80-90 C and then the reaction mixture wasplaced in an oil bath at 150 C for 2 h, the excess of oxychloridewas removed by distillation. The cooled reaction mixture waspoured in to water and made alkaline with ammonia solution.The product was filtered and washed with hot water [7].

References: [1]European Journal of Medicinal Chemistry,2020,vol. 192.
[2]Journal of the Chemical Society,1947,p. 759,761.
[3]Chemical Biology and Drug Design,2017,vol. 90,p. 926 - 935.
[4]Journal of Fluorescence,2019.

3
[ 54-60-4 ]
[ 330-83-6 ]

References: [1]Bulletin de la Societe Chimique de France,1951,p. 318,323.

4
[ 88-67-5 ]
[ 371-40-4 ]
[ 54-60-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With copper (I) iodide; copper atom; potassium carbonate; In N,N-dimethyl-formamide; for 2.0h;Inert atmosphere;	To a solution of 7 (1.00 g, 4.03 mmol) in DMF (15 mL) was added K2CO3 (1.11 g, 8.08 mmol), CuI (38 mg, 0.02 mmol), Cu (26 mg, 0.04 mmol) and 8a (974 mg, 0.61 mmol). The resulting solution was heated to 130 C under N2 for 2 h. After filtration through celite, the filtrate was diluted with EtOAc (150mL × 1) and washed with distd H2O (450 mL × 5). The organic layer was dried over Na2SO4, filtered and the solvent removed in vacuo. The residue was purified by silica gel chromatography (MeOH: CH2Cl2 = 0:100 - 2: 98) to give 9a (766 mg, 83%) as a solid. Mp 186-189 C. IR (KBr) 3335, 3052, 2868, 1652, 1578, 1509, 1258, 763 cm-1. 1H NMR (300 MHz, DMSO-d6) δ 13.04 (s, 1H), 9.53 (s, 1H), 7.89 (dd, J = 1.7, 7.9 Hz, 1H), 7.37 (td, J = 1.7, 7.8 Hz, 1H), 7.28 (m, 2H), 7.19 (m, 2H), 7.06 (dd, J = 0.9, 8.6 Hz, 1H), 6.76 (td, J = 0.9, 7.8 Hz, 1H). ESI-MS m/z: 230.1 (M-H)-.
	With copper atom; potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 20.0h;Schlenk technique; Inert atmosphere;	General procedure: A mixture of K2CO3 (1.0mmol, 1.0 eq), amine (1.2mmol, 1.2 eq), ortho-iodo benzoic acid (1.0mmol, 1.0 eq) and DMF (2.0mL) and copper powder (0.001mmol, 0.1% eq) were stirred in the schlenk tube for 12h at 100C under argon condition, and stopped heat and cooled to 25C. The solid (bottle green) was diluted with water, acidified with 2.0N HCl until pH 2 was adjusted. The black solid was precipitated and filtered. The filter cake was washed with an excess of water to remove the excess amine, dissolved in dichloromethane. The dichloromethan was concentrated by rotary evaporation under reduced pressure and dried over Na2SO4. The crude compounds, o-aminobenzoic acid derivatives, were obtained. Then o-aminobenzoic acid derivatives (1.0 eq), tryptamine (1.0 eq), EDCI·HCl (1.2 eq), HOBT (1.1 eq) were dissolved in dichloromethane (3mL), and Et3N (2.5 eq) was added at room temperature and stirred for 8h. After completion of the reaction detected by TLC, the reaction liquid was concentrated by rotary evaporation under reduced pressure. Then the resulting residue was purified by silica gel flash column chromatography to afford the desired product as a solid and the total yield was 49-95%.
	With copper atom; potassium carbonate; In N,N-dimethyl-formamide;Heating; Inert atmosphere;	General procedure: A mixture of 2-iodobenzoic acid 1 (1.0 mmol), anilines(1 mmol) 2, K2CO3 (2.0 mmol), and Cu powder (0.1 mmol) in DMF(3 mL) were added in a pressure vessel and stirred at 110 C for 12 hunder nitrogen. Then added 30 mL water to the cooled reactionmixture and filtrated through Celite. The filtrate was acidified withHCl (2 M), and precipitation can be observed. Then the insoluble crude product is obtained by filtration and purified by rinsing with5% aqueous Na2CO3 to afford the product 3

With copper atom; potassium carbonate; In N,N-dimethyl-formamide;Heating; Inert atmosphere;

General procedure: A mixture of 2-iodobenzoic acid 1 (1.0 mmol), anilines(1 mmol) 2, K2CO3 (2.0 mmol), and Cu powder (0.1 mmol) in DMF(3 mL) were added in a pressure vessel and stirred at 110 C for 12 hunder nitrogen. Then added 30 mL water to the cooled reactionmixture and filtrated through Celite. The filtrate was acidified withHCl (2 M), and precipitation can be observed. Then the insoluble crude product is obtained by filtration and purified by rinsing with5% aqueous Na2CO3 to afford the product 3

References: [1]European Journal of Medicinal Chemistry,2020,vol. 192.
[2]Journal of the Chemical Society,1947,p. 759,761.
[3]Journal of Organic Chemistry,2014,vol. 79,p. 7451 - 7458.
[4]European Journal of Medicinal Chemistry,2021,vol. 222.
[5]European Journal of Medicinal Chemistry,2022,vol. 228.
[6]Bioorganic and Medicinal Chemistry,2022,vol. 55.
[7]European Journal of Medicinal Chemistry,2022,vol. 228.

5
[ 54-60-4 ]
[ 18201-71-3 ]

References: [1]Journal of Medicinal Chemistry,1968,vol. 11,p. 111 - 117.

6
[ 17264-73-2 ]
[ 371-40-4 ]
[ 54-60-4 ]

References: [1]Journal of Medicinal Chemistry,1968,vol. 11,p. 111 - 117.

7
[ 50-00-0 ]
[ 54-60-4 ]
[ 180911-97-1 ]