Structure of 53947-84-5
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CAS No. : | 53947-84-5 |
Formula : | C10H9NO5 |
M.W : | 223.18 |
SMILES Code : | O=C(O)C1=CC=CC=C1NC(CC(O)=O)=O |
MDL No. : | MFCD00201912 |
Boiling Point : | No data available |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319 |
Precautionary Statements: | P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 |
* 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 toluene; for 0.5h;Heating / reflux; | Piperidine (100 mul_, 1.01 mmol) was added to a suspension of 3,4- bis(difluoromethoxy)benzaldehyde (240 mg, 1.01 mmol) and 2- [(carboxyacetyl)amino]benzoic acid (204 mg, 0.92 mmol) in toluene (5.0 mL). The <n="37"/>reaction flask was fitted with a Dean-Stark apparatus and heated to reflux for 30 min. The reaction was then cooled to rt and the resulting suspension was filtered and washed with toluene. The piperidinium salt was dissolved in MeOH (5 ml.) and water (2 ml.) and the solution was acidified with 50% aqueous AcOH. The crude product was collected by filtration and recrystallised from EtOH/water, filtered and washed with water to afford (E)-2-[[3,4-bis(difluoromethoxy)phenyl)-1-oxo-2-propenyl]amino]benzoic acid (259 mg, 71 %) as a colourless crystalline solid; mp 190-193 0C; deltaH (400 MHz, DMSO-Cf6) 6.96 (d, J = 15.6 Hz, 1 H, CH=CHCO), 7.18 (t, J3A = J4,5 = 8.0 Hz, 1 H, H4), 7.27 (t, J = 73 Hz, 1 H, OCHF2), 7.38 (d, J5-beta- = 8.0 Hz, 1 H, H5'), 7.61 (d, J = 15.6 Hz, 1 H, CH=CHCO), 7.62 (t, J4,5 = J5beta = 8.0 Hz, 1 H, H5), 7.78 (d, J2-beta- = 1.6 Hz, 1 H, HZ), 7.68 (dd, J5, 6' = 8.0, J2;& = 1.6 Hz, 1 H, H6'), 8.00 (d, J3A = 8.0 Hz, 1 H, H3), 8.69 (d, J5,6 = 8.0 Hz, 1 H, H6), 11.35 (s, 1 H, NH), 13.56 (br s, 1 H, CO2H); deltac (100 MHz, DMSO-Cf6) 116.3 (t, J = 258 Hz), 116.5 (t, J = 258 Hz), 117.0, 120.1 , 120.5, 120.8, 123.0, 123.8,126.7, 131.1 , 132.8, 133.9, 139.3, 140.7, 141.9, 142.7, 163.5, 169.4; HRMS (ESI") calculated for C18H13F4NO5 [M-H]" 398.0646, found 398.0652; vmax 1034, 1217, 1513,1604, 1683,2892,3466 cm"1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With piperidine; In toluene; for 0.5h;Reflux; | Piperidine (100 pL, 1.01 mmol) was added to a suspension of 3,4- bis(difluoromethoxy)benzaldehyde (240 mg, 1.01 mmol) and 2- [(carboxyacetyl)amino]benzoic acid (204 mg, 0.92 mmol) in toluene (5.0 mL). The reaction flask was fitted with a Dean-Stark apparatus and heated to reflux for 30 min. The reaction was then cooled to rt and the resulting suspension was filtered and washed with toluene. The piperidinium salt was dissolved in MeOH (5 mL) and water (2 ml.) and the solution was acidified with 50% aqueous AcOH. The crude product was collected by filtration and recrystallised from EtOH water, filtered and washed with water to afford (E)-2-[[3,4- bis(difluoromethoxy)phenyl)-1-oxo-2-propenyl]amino]benzoic acid (259 mg, 71%) as a colourless crystalline solid; mp 190-193 C; deltaEta (400 MHz, DMSO-d6) 6.96 (d, J = 15.6 Hz, 1 H, CH=CHCO), 7.18 (t, 3,4 = JA.S = 8.0 Hz, 1H, H4), 7.27 (t, J = 73 Hz, 2H, OCHF2), 7.38 (d, J5,6. = 8.0 Hz, 1 H, H5'), 7.61 (d, J = 15:6 Hz, 1 H, CH=CHCO), 7.62 (t, J4,5 = Js,e = 8.0 Hz, 1 H, H5), 7.78 (d, J2 = 1.6 Hz, 1 H, H2 7.68 (dd, JS - = 8.0, JZI6- = 1.6 Hz, 1 H, H6'), 8.00 (d, J3,4 = 8.0 Hz, 1H, H3), 8.69 (d, J5(6 = 8.0 Hz, 1H, H6), 11.35 (s, 1H, H), 13.56 (br s, 1H, C02H); 6C (100 MHz, DMSQ-o*6) 116.3 (t, J = 258 Hz), 116.5 (t, J = 258 Hz), 117.0, 120.1 , 120.5, 120.8, 123.0, 123.8, 126.7, 131.1 , 132.8, 133.9, 139.3, 140.7, 141.9, 142.7, 163.5, 169.4; HRMS (ESI) calculated for CieH13F4N05 [Mu-EtaGamma 398.0646, found 398.0652; 1034, 1217, 1513, 1604, 1683, 2892, 3466 cm-1. |
60% | With piperidine; In toluene; for 0.5h;Dean-Stark; Reflux; | Piperidine (5.00 mL, 51.0 mmol) was addedto a suspension of <strong>[127842-54-0]3,4-bis(difluoromethoxy)benzaldehyde</strong> (12) (11.0 g, 46.2 mmol) and 2-[(carboxyacetyl)amino]benzoic acid (7) (10.3 g, 46.2 mmol) in toluene (110mL). The reaction flask was fitted with a Dean-Stark apparatus and heated toreflux for 30 min. The reaction was then cooled to rt and the resultingsuspension was filtered and washed with toluene. The piperidinium salt wasdissolved in MeOH (100 mL) and water (25 mL) and the solution was acidifiedwith 1 M aqueous HCl and further diluted with water (100 mL). The crude productwas collected by filtration and recrystallised twice from EtOH/water, filteredand washed with water to afford (E)-2-[[3,4-bis(difluoromethoxy)phenyl)-1-oxo-2-propenyl]amino]benzoicacid (10.2 g, 60%) as a colourless crystalline solid;mp 196-198 C; deltaH (400 MHz, DMSO-d6) 6.96 (d, J = 15.6 Hz, 1H, CH=CHCO), 7.18 (t, J3,4 = J4,5= 8.0 Hz, 1H, H4), 7.27 (t, J = 73 Hz, 1H, OCHF2), 7.38 (d, J5?,6?= 8.0 Hz, 1H, H5?), 7.61 (d, J = 15.6 Hz, 1H, CH=CHCO), 7.62 (t, J4,5= J5,6 = 8.0 Hz, 1H, H5), 7.78 (d, J2?,6? = 1.6 Hz, 1H, H2?),7.68 (dd, J5?,6? = 8.0, J2?,6? = 1.6 Hz, 1H, H6?), 8.00 (d, J3,4 = 8.0 Hz, 1H, H3),8.69 (d, J5,6 = 8.0 Hz,1H, H6), 11.35 (s, 1H, NH), 13.56 (br s, 1H, CO2H); deltaC (100 MHz, DMSO-d6) 116.3 (t, J = 258 Hz), 116.5 (t, J = 258 Hz), 117.0, 120.1, 120.5, 120.8,123.0, 123.8, 126.7, 131.1, 132.8, 133.9, 139.3, 140.7, 141.9, 142.7, 163.5,169.4; HRMS (ESI-) calculated for C18H13F4NO5[M-H]- 398.0646, found 398.0652; nmax 1034, 1217, 1513, 1604, 1683,2892, 3466 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With piperidine; In toluene; for 0.5h;Dean-Stark; Reflux; | Piperidine (0.12 mL, 1.2 mmol) was added toa solution of 3-trifluoromethoxy-4-methoxybenzaldehyde (0.26g, 1.2 mmol) and 2-[(carboxyacetyl)amino]benzoic acid (7) (0.25 g, 1.1 mmol) in toluene (5 mL). The reaction flask wasfitted with a Dean-Stark apparatus and heated to reflux for 30 min. Thereaction was then cooled to rt and the resulting suspension was filtered andwashed with toluene. The piperidinium salt was dissolved in MeOH (5 mL) andwater (2 mL) and the solution was acidified with 20% aqueous AcOH. Theprecipitate was filtered and the crude product was recrystallised fromEtOH/water affording (E)-2-[[3-(3-fluoro-4-trifluoromethoxyphenyl)-1-oxo-2-propenyl]amino]benzoicacid (0.27 g, 66%) as a pale yellow crystalline solid;mp 264-266 C; deltaH (500 MHz, DMSO-d6) 7.02 (d, J = 15.6 Hz, 1H, CH=CHCO), 7.18 (t, J3,4 = J4,5= 8.0 Hz, 1H, H4), 7.58-6.82 (m, 4H, H3, H5,H5?, H6?), 7.98-8.01 (m, 2H, H2?,CH=CHCO), 8.61 (d, J5,6 = 8.0 Hz, 1H, H6), 11.37 (s, 1H, NH), 13.61 (br s, 1H, CO2H); deltaC (125 MHz, DMSO-d6) 116.5 (d, J= 19 Hz), 116.8, 120.0 (q, J = 256Hz), 120.4, 123.0, 124.2, 125.2, 125.7, 131.1, 134.0, 135.8 (d, J = 13 Hz), 136.1, 138.7, 140.6, 153.7(d, J = 249 Hz), 163.3, 169.4; HRMS(ESI) calculated for C17H11F4NO4[M+H]+ 370.0697, found 370.0696; nmax 754, 1168, 1250, 1584, 1659, 1677,2874, 3064, 3312 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With piperidine; In toluene; at 110℃; for 10h; | To a mixture of 2-[(2-carboxyacetyl)amino]benzoic acid (500 mg, 2.24 mmol, 1.0 equiv.) and <strong>[43192-34-3]4-bromo-3-methoxy-benzaldehyde</strong> (530 mg, 2.46 mmol, 1.1 equiv.) in toluene (5 mL) was added piperidine (19 mg, 0.224 mmol, 0.1 equiv.). The mixture was stirred at 110°C for 10 hours. The precipitated solid was collected by filtration and suspended in IN hydrochloric acid (20 mL) and stirred at 20°C for 2 hours. The mixture was filtered and the collected solid dried under vacuum to afford the desired product as a yellow solid (400 mg, 47percent). 1H NMR(400 MHz, DMSO-d6) delta 11.34 (s, 1H), 8.61 ((d, J = 8.0 Hz, 1H), 8.02 (dd, 1.2 Hz, 7.6 Hz, 1H), 7.63 - 7.59 (m, 3H), 7.50 (s, 1H), 7.27 (d, J = 8.0 Hz, 1H), 7.19 (t, J = 8.0 Hz, 1H), 7.02 (d, J = 8.0 Hz, 1H), 3.93 (s, 3H). |
Tags: 53947-84-5 synthesis path| 53947-84-5 SDS| 53947-84-5 COA| 53947-84-5 purity| 53947-84-5 application| 53947-84-5 NMR| 53947-84-5 COA| 53947-84-5 structure
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