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Product Details of [ 2765-91-5 ]

CAS No. :	2765-91-5	MDL No. :	MFCD01661985
Formula :	C₁₅H₁₂F₃NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	295.26	Pubchem ID :	-
Synonyms :

Safety of [ 2765-91-5 ]

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Application In Synthesis of [ 2765-91-5 ]

* 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.

Upstream synthesis route of [ 2765-91-5 ]
Downstream synthetic route of [ 2765-91-5 ]

[ 2765-91-5 ] Synthesis Path-Upstream 1~1

1
[ 2765-91-5 ]
[ 530-78-9 ]

Yield	Reaction Conditions	Operation in experiment
55%	With water; potassium hydroxide In ethanol at 100℃; Inert atmosphere	To a solution of the methyl ester (1 equiv) in EtOH (0.2 M) was added KOH (2 equiv per ester) in water (0.2 M) at room temperature. The reaction mixture was allowed to stir at 100 °C for 1-6 h. Once the reaction appeared complete by TLC analysis, EtOH was evaporated from the reaction mixture, the resultant solution was cooled to 0 °C and acidified to pH 2 w 2M aq HCl. The resultant precipitated product was collected by vacuum filtration and washed with water.
55%	With water; potassium hydroxide In ethanol at 100℃;	General procedure: To a solution of the methyl ester (1 equiv) in EtOH (0.2 M)was added KOH (2 equiv per ester) in water (0.2 M) at roomtemperature. The reaction mixture was allowed to stir at 100°C. for 1-6 h. Once the reaction appeared complete by TLC analysis, EtOH was evaporated from the reaction mixture, the resultant solution was cooled to 0° C. and acidified to pH 2w 2M aq Rd. The resultant precipitated product was collected by vacuum filtration and washed with water. Reaction of flufenamic acid methyl ester according to general procedure B provided flufenamic acid (Compound 1) as a white solid (55percent yield). ¹H NMR (DMSO, 500 MHz): δ=13.14 (bs, 1H), 9.66 (s, 1H), 7.93 (d, J=7.9 Hz, 1H), 7.40-7.60 (m, 4H), 7.25-7.36 (m, 2H), 6.89 (t, J=7.5 Hz, 1H). ¹³C NMR (DMSO, 125 MHz): δ=169.5, 145.4, 142.0, 134.1, 131.9, 130.5, 123.7, 118.9, 118.5, 116.3, 114.9, 114.5. HRMS (ES) Calcd. for C₁₄H₁₀F₃NO₂: 280.0585 (M-H^-). found 280.0590 (M-H^-).

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 5, p. 1464 - 1468
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2311 - 2323
[3] Patent: US9271961, 2016, B2, . Location in patent: Page/Page column 58; 59
[4] Patent: US5462952, 1995, A,

[ 2765-91-5 ] Synthesis Path-Downstream 1~3

1
[ 67-56-1 ]
[ 530-78-9 ]
[ 2765-91-5 ]

Reference： [1]Archiv der Pharmazie,1984,vol. 317,p. 595 - 606
[2]Farmaco, Edizione Scientifica,1975,vol. 30,p. 276 - 286
[3]Journal of Pharmacy and Pharmacology,1980,vol. 32,p. 795 - 796
[4]Molecules,2011,vol. 16,p. 3544 - 3551

2
[ 2765-91-5 ]
[ 530-78-9 ]

Yield	Reaction Conditions	Operation in experiment
55%	With water; potassium hydroxide; In ethanol; at 100℃;Inert atmosphere;	To a solution of the methyl ester (1 equiv) in EtOH (0.2 M) was added KOH (2 equiv per ester) in water (0.2 M) at room temperature. The reaction mixture was allowed to stir at 100 C for 1-6 h. Once the reaction appeared complete by TLC analysis, EtOH was evaporated from the reaction mixture, the resultant solution was cooled to 0 C and acidified to pH 2 w 2M aq HCl. The resultant precipitated product was collected by vacuum filtration and washed with water.
55%	With water; potassium hydroxide; In ethanol; at 100℃;	General procedure: To a solution of the methyl ester (1 equiv) in EtOH (0.2 M)was added KOH (2 equiv per ester) in water (0.2 M) at roomtemperature. The reaction mixture was allowed to stir at 100C. for 1-6 h. Once the reaction appeared complete by TLC analysis, EtOH was evaporated from the reaction mixture, the resultant solution was cooled to 0 C. and acidified to pH 2w 2M aq Rd. The resultant precipitated product was collected by vacuum filtration and washed with water. Reaction of flufenamic acid methyl ester according to general procedure B provided flufenamic acid (Compound 1) as a white solid (55% yield). 1H NMR (DMSO, 500 MHz): delta=13.14 (bs, 1H), 9.66 (s, 1H), 7.93 (d, J=7.9 Hz, 1H), 7.40-7.60 (m, 4H), 7.25-7.36 (m, 2H), 6.89 (t, J=7.5 Hz, 1H). 13C NMR (DMSO, 125 MHz): delta=169.5, 145.4, 142.0, 134.1, 131.9, 130.5, 123.7, 118.9, 118.5, 116.3, 114.9, 114.5. HRMS (ES) Calcd. for C14H10F3NO2: 280.0585 (M-H-). found 280.0590 (M-H-).
	With hydrazine hydrate; In methanol;	Preparation 7 2-[(3-Trifluoromethylphenyl)amino]-benzoic acid, hydrazide Hydrazine hydrate (14 ml) is added dropwise to a solution of methyl 2-[(3-trifluoromethylphenyl)amino]-benzoate (1.463 g, 4.95 mmol) in 70 ml of methanol. The reaction solution is heated at 60 C. under an inert atmosphere for two hours and then concentrated in vacuo and chromatographed, eluding with ethyl acetate and hexane (1:1), providing 763.0 mg (52%) of a white solid, mp 134-135 C. Anal. for C14 H12 F3 N3 O requires: C, 56.95; H, 4.10; F, 19.30; N, 14.23 Found: C, 56.93; H, 4.21; F, 19.17; N, 14.18

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1464 - 1468
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 2311 - 2323
[3]Patent: US9271961,2016,B2 .Location in patent: Page/Page column 58; 59
[4]Patent: US5462952,1995,A

3
[ 530-78-9 ]
[ 2765-91-5 ]

Yield	Reaction Conditions	Operation in experiment
71%	With sulfuric acid; In methanol;	EXAMPLE 28 2-[[3-(Trifluoromethyl)phenyl]amino]benzoic acid, methyl ester Reaction of 2-[[3-(trifluoromethyl)phenyl]amino]benzoic acid with methanol and sulfuric acid according to the procedure of Example 26 gives a 71% yield of 2-[[3-(trifluoromethyl)phenyl]amino]benzoic acid, methyl ester as a colorless oil.

Reference： [1]Patent: US4981865,1991,A

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[ CAS No. 2765-91-5 ] {[proInfo.proName]}

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[ 2765-91-5 ] Synthesis Path-Upstream 1~1

[ 2765-91-5 ] Synthesis Path-Downstream 1~3

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