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CAS No. : | 92-70-6 | MDL No. : | MFCD00004103 |
Formula : | C11H8O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ALKYHXVLJMQRLQ-UHFFFAOYSA-N |
M.W : | 188.18 | Pubchem ID : | 7104 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 52.93 |
TPSA : | 57.53 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.28 cm/s |
Log Po/w (iLOGP) : | 1.41 |
Log Po/w (XLOGP3) : | 3.05 |
Log Po/w (WLOGP) : | 2.24 |
Log Po/w (MLOGP) : | 2.02 |
Log Po/w (SILICOS-IT) : | 1.84 |
Consensus Log Po/w : | 2.11 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.39 |
Solubility : | 0.0765 mg/ml ; 0.000407 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.92 |
Solubility : | 0.0224 mg/ml ; 0.000119 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.87 |
Solubility : | 0.252 mg/ml ; 0.00134 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.01 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P501-P273-P272-P260-P270-P202-P201-P264-P280-P337+P313-P305+P351+P338-P308+P311-P362+P364-P333+P313-P301+P312+P330-P302+P352+P312-P405 | UN#: | N/A |
Hazard Statements: | H302+H312-H315-H319-H361-H371-H317-H412 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
91% | at 120℃; for 3 h; | 1L three-necked flask,3-hydroxy-2-naphthoic acid (50 g, 0.27 mol)And 600 mL of glacial acetic acid, stirred and dissolved.Bromine (34 mL, 0.67 mol) was treated with 100 mLGlacial acetic acid diluted, slowly dropping into the reaction solution,Keep the temperature 20-30 ° C.After completion of the dropwise addition, the temperature was raised to 120 ° C,Reflux 3h. Stop heating,Naturally cooled to room temperature,The reaction solution was poured into 3000 mL of ice water,Precipitation of a large number of yellow solid,Filter, filter cake with water,Oven drying,To give 84 g of intermediate 2 as a solid, 91percent yield. |
90% | at 20 - 125℃; for 10 h; | In a 1 L three-necked bottle, 50g of 3-hydroxy-2-naphthoic acid (0.27mol) and 600ml of glacial acetic acid wereadded, and the mixture was stirred to be a solution. 34ml of bromine element (0.67mol) was diluted with 100ml of glacialacetic acid, slowly added dropwise to the reaction mixture, and the temperature was kept at 20-30°C. After the end ofdropwise addition, the temperature was elevated to 125°C, and refluxed for 10h. The heating was stopped, and themixture was stirred, and slowly cooled to room temperature to precipitate a large amount of a solid. The solid was filteredoff, and the filter cake was washed with water (200ml*2), and dried in an oven to obtain 82.75g of the solid with a yieldof 90percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.5% | With potassium carbonate In acetone at 0 - 10℃; for 4h; Reflux; Inert atmosphere; | 10.1 (1) Preparation of methyl 2-methoxy-3-naphthoate 10.0 g (0.055 mol) of 2-hydroxy-3-naphthoic acid was weighed out, was added to 250 mL of a three-neck flask equipped with a stir bar, Add 100mL acetone stirring until the raw materials dissolved, Slowly add anhydrous K2C03 18. 4g (0. 133m0l) control the internal temperature of 0 ° C, 11.6 mL (0.122 mol) of dimethyl sulfate was slowly added dropwise, The argon was added during the dropwise addition, So that the internal temperature is less than 10 ° C. Drop Bi, After slowly heating to reflux for 4 h, the reaction was complete by TLC, dropping to room temperature, and adding 10 mL of water to destroy unreacted dimethyl sulfate. Reaction solution appears a lot of viscous solid, stirring lh after suction filtration, The filter cake was washed with a small amount of acetone, The filtrate was concentrated, The resulting residue was extracted with CH2Cl2 and H20, Dried and concentrated to give the product 11. 2g, yield 97. 5%. |
88% | With potassium carbonate In acetone for 12h; Reflux; | |
81% | With potassium carbonate In acetone for 10h; Reflux; | Methyl 7-bromo-3-methoxy-2-naphthoate (4a). General procedure: In 2 L three-necked bottle, 7-bromo-3-hydroxy-2- naphthoic acid (3, 112g, 0.42mol) was suspended in acetone (1 L). To this mechanically stirred mixture was added anhydrous potassium carbonate (288g, 2.08mol) and dimethyl sulfate (99mL, 1.05mol). The reaction was refluxed for about 10h, then cooled to room temperature and water (50mL) was added stirred for 2h to destroy any remaining dimethyl sulfate. The inorganic material was filtered and the acetone was removed under reduced pressure. The residue was taken up in methylene chloride, washed several times with water, dried over anhydrous magnesium sulfate, filtered, concentrated and recrystallized in ethyl acetate and petroleum ether to afford white product (105.6g, 86%). |
With potassium hydroxide | ||
With potassium carbonate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; | Pamoic acid may be prepared by condensing commercially available 3 -hydroxy-2 -naphthoic acid (Acros Organics, Fairlawn, NJ) with formaldehyde or paraformaldehyde in the presence of sodium hydroxide (Strohbach, 1901, Chem. Ber. 34:4148; Hosaeus, 1892, Chem. Ber.25:3215; Brass, 1928, Chem. Ber. 61 :1001), as shown in Scheme I. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70.6% | With sulfuric acid; for 6h;Reflux; | To a round bottom flask were added 5 g 3-hydroxy-2-naphthalic acidand 16 mL ethanol. The reaction mixture was refluxed for 6 h. After thecompletion of the reaction, the reaction mixture was cooled down to room temperature and washed with distilled water. The organic layerwas recovered and washed with saturated sodium bicarbonate followedby drying with anhydrous MgSO4. The MgSO4 was removed by filtrationand the filtrate was dried under reduced pressure. The resulted solid waspurified by silica chromatography with petroleum ether and ethyl acetate(10:1, v/v) as eluent to give the compound ethyl 3-hydroxy-2-naphthoate(4.1229 g, yield 70.60%). Melting point: 83-84 C. 1H NMR(500 MHz, CDCl3, ): 10.58 (s, 1H), 8.49 (s, 1H), 7.81 (d, J 8.3 Hz,1H), 7.69 (d, J 8.4 Hz, 1H), 7.51 (t, J 7.6 Hz, 1H), 7.36-7.30 (m,2H), 4.49 (q, J 7.1 Hz, 2H), 1.50 (t, J 7.1 Hz, 3H).13C NMR (126MHz, CDCl3, ): 169.91, 156.44, 137.87, 132.32, 129.20, 129.06,127.02, 126.28, 123.86, 114.43, 111.62, 61.80, 14.25. HRMS (ESI) m/zcalculated for C13H12O3Na(MNa) 239.06787, found 239.06760. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 220℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In water; chlorobenzene; toluene; at 85℃; for 5h; | 1. 1 part of the material 2-hydroxy-3-naphthoic acid (the amount of the substance,The same below) dissolved in water and immiscible solvent 1.1 (such as toluene, chlorobenzene),The solution was added to the reactor (Figure 1),Then, 1.15 parts of 2,5-dimethoxy-4-chloroaniline was added,The reaction mixture was heated at a temperature of 85 C,The reaction time was 5h, and the crude product was obtained in 89% yield.2. Distillation of crude products, the yield of 94%.3. Add the refined product to a separate dryer (Figure 2)The rising steam is evenly contacted with the crude phenol concentrate through the steam distributor,Water vapor cold liquid liquefaction into small water droplets, dissolved products in the soluble impurities,Excessive steam is condensed at the top of the condenser to form a stream of water into the desiccator to rinse the phenolic AS-LC product,After repeated rinsing three times, finally, in the jacket outside the dryer through the water vapor,The dryer was dried by heating to give the final product in a yield of 92%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With bromine; acetic acid; at 120℃; for 3h; | 1L three-necked flask,3-hydroxy-2-naphthoic acid (50 g, 0.27 mol)And 600 mL of glacial acetic acid, stirred and dissolved.Bromine (34 mL, 0.67 mol) was treated with 100 mLGlacial acetic acid diluted, slowly dropping into the reaction solution,Keep the temperature 20-30 C.After completion of the dropwise addition, the temperature was raised to 120 C,Reflux 3h. Stop heating,Naturally cooled to room temperature,The reaction solution was poured into 3000 mL of ice water,Precipitation of a large number of yellow solid,Filter, filter cake with water,Oven drying,To give 84 g of intermediate 2 as a solid, 91% yield. |
90% | With bromine; acetic acid; at 20 - 125℃; for 10h; | In a 1 L three-necked bottle, 50g of 3-hydroxy-2-naphthoic acid (0.27mol) and 600ml of glacial acetic acid wereadded, and the mixture was stirred to be a solution. 34ml of bromine element (0.67mol) was diluted with 100ml of glacialacetic acid, slowly added dropwise to the reaction mixture, and the temperature was kept at 20-30C. After the end ofdropwise addition, the temperature was elevated to 125C, and refluxed for 10h. The heating was stopped, and themixture was stirred, and slowly cooled to room temperature to precipitate a large amount of a solid. The solid was filteredoff, and the filter cake was washed with water (200ml*2), and dried in an oven to obtain 82.75g of the solid with a yieldof 90%. |
At room temperature, a suspension of 3-hydroxy-2-naphthoic acid 1 (50 g, 266 mmol) in acetic acid (500 mL) was mechanically stirred for 10 min. A solution of bromine (34 mL, 665 mmol) in acetic acid (200 mL) was then added dropwise through a dropping funnel. Then the mixture was heated to reflux for 3 h. After cooling to room temperature, the reaction was quenched with 3000 mL of ice water. The yellow solid was filtered and dried to give a crude product of 2 (84 g, 91 %) as a yellow solid. 1H-NMR (400 MHz, DMSO-d6): delta = 3.63 (br. s), 7.84 (dd, J = 9.2, 2.0 Hz, 1H), 7.98 (d, J = 9.0 Hz, 1H), 8.41 (d, J = 2.0 Hz, 1H), 8.63 (s, 1H) ppm. HRMS (ESI): [M + H]-, found 344.8591. C11H5Br2O3 requires 344.8585. |
With bromine; acetic acid; for 1.5h;Reflux; | A solution of bromine (6.84 mL, 133 mmol) in acetic acid (50 mL) was added dropwise to a solution of 3-hydroxy-2-naphthoic acid (10 g, 53.1 mmol) in acetic acid (150 mL) over 30 min. After the addition the reaction was heated to reflux for 1 hr, cooled to RT and poured into ice water. The solid product was filtered, washed with water and air dried to give a yellow solid. LCMS(m/z)= 345 [M-1]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With potassium carbonate In N,N-dimethyl-formamide at 80℃; Inert atmosphere; | |
96% | With potassium carbonate In N,N-dimethyl-formamide at 80℃; Inert atmosphere; | 3 Methyl 3-methoxy-2-naphthanoate (S8) Adapted from [4] 3-hydroxy-2- naphthanoic acid (5.0 g, 26.6 mmol, 1.0 eq) and K2CO3 (14.7 g, 106.3 mmol, 4.0 eq) were added to a 250 ml_ round bottom flask. The flask was evacuated to 150 mtorr and back filled with nitrogen gas three times. Anhydrous DMF (60 ml_) was then added and stirred in the round bottom flask. Mel (8.60 ml_, 138.2 mmol, 5.2 eq) was added to the flask and the mixture was heated to 80 °C for 24 h. After which the vessel was cooled to room temperature and the excess carbonate was quenched by the addition of 3 M H2SO4. The solution was then diluted to 500 mL using Dl water. The solution was extracted with EtOAc (x3). The combined organic extracts were rinsed with 75 mL of 2 M LiCI (x1 ), 175 mL water (x3), and brine (x1 ) after which the EtOAc was dried over Na2S04 and filtered. The ethyl acetate was removed using a rotary evaporator and the crude product was subjected to column chromatography, (S1O2, 7% v/v (0302) EtOAc/hexanes). Yield 5.48 g (96%). (0303) Figure 39 shows 1HNMR (400 MHz, CDCI3, 25°C) d (ppm) 8.30 (s, 1 H), 7.81 (d, J = 8.9 Hz, 1 H), 7.73 (d, J = 9.0 Hz, 1 H), 7.51 (t, J = 8.2 Hz, 1 H), 7.37 (t, J = 8.1 Hz, (0304) 1 H), 7.20 (s, 1 H), 3.98 (d, J = 15.4 Hz, 6H) spectra of compound S8. (0305) Figure 40 shows 13C NMR (101 MHz, CDCI3, 25°C) d (ppm) 166.80, 155.81 , 136.20, 132.89, 128.79, 128.52, 127.62, 126.55, 124.50, 121.80, 106.88, 77.16, 56.09, 52.38 spectra of compound S8. |
92% | With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 96h; |
Stage #1: 3-Hydroxy-2-naphthoic acid With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃; for 10h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide; calcium chloride; sodium nitrite; In water; | EXAMPLE 1 A solution of 24.2 grams (0.1294 mole) of pure 6-amino-m-toluenesulfonic acid and 1.2 grams (0.0054 mole) of 2-naphthylamine-1-sulfonic acid is prepared in 500 ml of water by adding 57 ml of a 10% solution of sodium hydroxide and adjusting the pH to 11.5. A solution of 35.6 grams of calcium chloride and 1.5 grams of strontium nitrate in 100 ml of water is added thereto and the mixture cooled to 0 C. with ice. The amines are diazotized by adding 35 ml (0.14 mole) of 4 N sodium nitrite, followed by 150 ml (0.411 mole) of 10% hydrochloric acid. The mixture is stirred for about 3 minutes at 0 C., while maintaining excess nitrous acid. 2-Hydroxy-3-naphthoic acid (28.0 grams, 0.1489 mole) is dissolved in 500 ml of water by adding 180 ml of 10% sodium hydroxide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; at 25 - 50℃; for 20.0h; | Example 7; Preparation of Imipramine XinafoateTo a solution containing 7.7 g of 3-hydroxy-2-napthoic acid in 75.0 g of USP water was added as necessary dilute HCl or NaOH solution to adjust the solution to about pH 9.4. To a second solution of 13.6 g of <strong>[113-52-0]imipramine HCl</strong> in 100.0 g of USP water was added as necessary dilute HCl or NaOH solution to adjust the solution to about pH 4.5. The <strong>[113-52-0]imipramine HCl</strong> solution was added to the 3-hydroxy-2-napthoic sodium salt solution over a period of about 2 h. The mixture was stirred and held at around 50 C. for at least 18 h. The mixture was cooled to below 25 C. and the solids were collected by filtration. The solid cake was washed with USP water (2×100 g). The solid cake was dried at 105 C. under vacuum to yield a powder (12.7 g) and characterized by DSC (FIG. 13), FTIR (FIG. 14) and 1H NMR (FIG. 15). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(Example 1) 34.80 parts of 4-aminotoluene-3-sulfonic acid (purity: 98.00%) was dispersed in 50 parts of water, 22.1 parts of 35% hydrochloric acid was added, ice and water were added, and with the temperature held at 0C, 32.4 parts of a 40% aqueous solution of sodium nitrite was added in a single batch, thereby yielding 650 parts of a suspension containing a diazo component. Next, 34.98 parts of 3-hydroxy-2-naphthoic acid (purity: 98.50%) was dispersed in 400 parts of 50C water, 69 parts of a 25% aqueous solution of caustic soda was added and dissolved, and ice and water were then added, thus forming 980 parts of a 10C aqueous solution containing a coupler component. The total quantity of this aqueous solution containing the coupler component was placed inside a circular cylindrically shaped agitating tank 5 with an internal capacity of 2 liters, a rotational axis 1 fitted with each of the agitating blades shown in FIG. 1 was positioned within the center of the agitating tank 5, and the rotational axis 1 was then fixed to a motor, thereby completing the setup of the agitator. Subsequently, the rotational axis 1 was rotated at a rotational rate of 100 rpm, and with the aqueous solution containing the coupler component undergoing constant agitating, the total quantity of the aforementioned suspension containing the diazo component was added in a single batch. The reaction temperature was maintained at 10C to 15C. After 10 minutes, completion of the coupling reaction was confirmed using the H acid color test described below. Subsequently, 147 parts of an aqueous solution of a 10% disproportionated rosin sodium salt was added, and following agitating for a further 60 minutes, the pH was adjusted to 12.5, yielding an azo dye suspension. In Example 1, the molar ratio of 4-aminotoluene-3-sulfonic acid : the 3-hydroxy-2-naphthoic acid was set to 1.000 : 1.005. To the agitating tank 5 containing the azo dye suspension was added 80 parts of a 35% aqueous solution of calcium chloride, and the resulting mixture was stirred for 60 minutes to complete the laking reaction, thus yielding a suspension containing a C.I. Pigment 57:1. This suspension was aged by agitating for 90 minutes at a temperature of 80C. In both the laking step and the heating step, the rotational rate of the agitating blades was set to the same rate as that used in the coupling reaction, and the coupling reaction, the laking reaction and the heating were conducted consecutively in the same agitating tank 5, with no change of the tank. Ice was then added, the liquid temperature was cooled to 60C, and hydrochloric acid was used to adjust the pH to a value of 8.5. Subsequently, the product was filtered, washed with water, dried for 10 hours at 100C, and then pulverized, yielding 93 parts of a dried pigment powder of the C.I. Pigment 57:1; (Example 2) With the exception of setting the molar ratio of 4-aminotoluene-3-sulfonic acid : 3-hydroxy-2-naphthoic acid (molar ratio) to 1.000 : 1.002, production was conducted in the same manner as Example 1, yielding 93 parts of a dried pigment powder.; (Example 3) With the exception of setting the molar ratio of 4-aminotoluene-3-sulfonic acid : 3-hydroxy-2-naphthoic acid to 1.000 : 1.003, production was conducted in the same manner as Example 1, yielding 93 parts of a dried pigment powder.; (Comparative Example 1) The molar ratio of 4-aminotoluene-3-sulfonic acid : 3-hydroxy-2-naphthoic acid was set to 1.000 : 1.005, and a suspension containing a diazo component and an aqueous solution containing a coupler component were prepared. The aqueous solution containing the coupler component was added into a circular cylindrically shaped reaction apparatus with an internal capacity of 2 liters and the agitating blades shown in FIG. 2, which was similar to the one in Example 1, and the suspension containing the diazo component was then added thereto while the agitating blades were rotated at a rotational rate of 300 rpm. The reaction temperature was maintained at 10C to 15C. After 60 minutes, the coloring was conducted using the H acid color test, 147 parts of an aqueous solution of a 10% disproportionated rosin sodium salt was added without completion of the coupling reaction, and following agitating for a further 60 minutes, the pH was adjusted to 12.5, yielding an azo dye suspension. The laking and heating were conducted using this azo dye suspension in the same manner as Example 1, yielding 92 parts of a dried pigment powder of the C.I. Pigment 57:1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Comparative Example 1; Synthesis of Pigment Red 57:1 by a Two-Step Procedure; Step 1: Synthesis of Lithol Rubine Potassium Salt, a Dye Precursor for Pigment Red 57:1; Diazotization: Into a 500 mL round bottom flask equipped with a mechanical stirrer, thermometer, and addition funnel was dissolved 2-amino-5-methylbenzenesulfonic acid (8.82 g, 47.1 mmol) into 0.5M KOH aqueous solution (97.0 mL). A medium brown solution was formed, which was cooled to between 0 C. and 2 C. A 20 wt % aqueous solution of sodium nitrite (NaNO2; 3.28 g, 47.6 mmol dissolved into 25 mL water) was added slowly to the first solution, maintaining the temperature below 3 C., which resulted in a red-brown solution. Concentrated HCl (10 M, 14.15 mL, 141.5 mmol) was then added dropwise while maintaining the internal temperature below 2 C. The mixture formed a light brown suspension. After complete addition of conc. HCl, the suspension was stirred an additional 30 min.Coupling: In a separate 2-L resin kettle was dissolved 3-hydroxy-2-naphthoic acid (8.86 g, 47.1 mmol) into an aqueous solution of KOH (8.72 g, 155.4 mmol) in water (95 mL). Additional water was added (250 mL), and the light-brown solution was then cooled to about 15 C. while stirring vigorously. The cold suspension of the diazonium salt solution from Step A was then transferred slowly into the coupling solution of Step B, while mixing vigorously. The color changed from dark red solution, to ultimately a yellowish-red (orange) slurry of precipitated colorant. The mixture was stirred for another 2 hours at room temp, then vacuum-filtered and diluted with water (500 mL) to provide an orange aqueous slurry of Lithol Rubine Dye Potassium salt, with approximate solids content of about 1.6%-wt. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In a manner known per se in the art, 3-hydroxy-2-naphthoic acid (60 parts) was converted into an acid chloride with thionyl chloride (40 parts) in nitrobenzene (400 parts), <strong>[20103-09-7]2,5-dichloro-1,4-phenylenediamine</strong> (25 parts) was added, and the resulting mixture was heated at 130 to 135C for 5 hours. Subsequent to cooling, methanol (200 parts) was added. The resulting precipitate was collected by filtration, washed with methanol and then with water, and dried to obtain a reactant (60 parts). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE ADispersant VIa) Diazo (Mixture 1):89.6 parts of 2-amino-4-chloro-5-methylbenzenesulfonic acid are dissolved in 400 parts of water and 41 parts of aqueous sodium hydroxide solution (w=33%). Diazotization is carried out with 162 parts of hydrochloric acid (w=31%) and 73 parts of sodium nitrite solution (w=40%) at 10 C. Then 50 parts of sodium acetate are added to establish a pH of 3-4.b) Coupler (Mixture 2):In 1600 parts of water and 98 parts of 33% strength aqueous sodium hydroxide solution, 79 parts of BONS (3-hydroxynaphthalene-2-carboxylic acid) are dissolved. The solution is cooled to 10 C. by addition of ice.c) Coupling:Mixture 1 is added in 90 minutes at 15 C. to mixture 2. Stirring is carried out first at 30 C. for an hour and then at 60 C. for an hour. The resulting deep-red suspension is filtered and the filter product is washed and dried in a forced-air drying oven at 80 C. This gives 160 parts of dispersant (VI). | ||
175Kg 2-chloro-4-aminotoluene-5-sulfonic acid was added to a conventional reaction kettle, 2000Kg of water was added; 215Kg of 30% hydrochloric acid was rapidly added, And then slowly at 6 C by adding 20% sodium nitrite solution 262Kg for diazotization stirring reaction for 1 hour;140Kg 3-hydroxy-2-naphthoic acid was poured into a coupling reactor, 250Kg of a 30% caustic soda was added, stirred to 3-hydroxy-2-naphthoic acid and 50kg of stearic acid was added;The diazonium solution was added to the coupling reactor at 12 C for coupling reaction, and the diazonium solution was added and stirred for 1. 5 hours.The temperature was raised to 42 C, 320Kg of calcium chloride was injected into the coupling reactor, stirred for 15 minutes, the post-treatment was heated to 85 C, incubated for 25 minutes, filtered and dried at 80 C to obtain a pigment weight of 382 kg , The pigment red Application performance: Resistant level 5, acid resistance 5, alkali 5, weather resistance 5, heat 220C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With phosphorus trichloride; In chlorobenzene; at 130℃; for 0.25h; | General procedure: 3-Hydroxynaphthalene-2-carboxylic acid (5.3 mmol) and the appropriate alkoxyaniline (5.3 mmol) were suspended in dry chlorobenzene (25 mL). Phosphorous trichloride (0.23 mL, 2.7 mmol) was added dropwise, and the reacting mixture was heated in the microwave reactor at maximal allowed power 500 W and 130C, using infrared flask-surface control of temperature, for 15 min. The solvent was evaporated under reduced pressure and the solid residue washed with 50 mL of 2 M HCl. The crude product was recrystallized from aqueous ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With phosphorus trichloride; In chlorobenzene; at 130℃; for 0.25h; | General procedure: 3-Hydroxynaphthalene-2-carboxylic acid (5.3 mmol) and the appropriate alkoxyaniline (5.3 mmol) were suspended in dry chlorobenzene (25 mL). Phosphorous trichloride (0.23 mL, 2.7 mmol) was added dropwise, and the reacting mixture was heated in the microwave reactor at maximal allowed power 500 W and 130C, using infrared flask-surface control of temperature, for 15 min. The solvent was evaporated under reduced pressure and the solid residue washed with 50 mL of 2 M HCl. The crude product was recrystallized from aqueous ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With phosphorus trichloride; In chlorobenzene; at 130℃; for 0.25h; | General procedure: 3-Hydroxynaphthalene-2-carboxylic acid (5.3 mmol) and the appropriate alkoxyaniline (5.3 mmol) were suspended in dry chlorobenzene (25 mL). Phosphorous trichloride (0.23 mL, 2.7 mmol) was added dropwise, and the reacting mixture was heated in the microwave reactor at maximal allowed power 500 W and 130C, using infrared flask-surface control of temperature, for 15 min. The solvent was evaporated under reduced pressure and the solid residue washed with 50 mL of 2 M HCl. The crude product was recrystallized from aqueous ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at -15 - 20℃;Inert atmosphere; | General procedure: 3-Hydroxy-2-naphthoic acid (1.0g, 5.31mmol) was dissolved in dry THF (10mL). The mixture was cooled to -15C, then N-(3-dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (EDCI) (1.53g, 7.965mmol), and HOBt (0.83g, 5.416mmol) were added. A solution of (2S)-2-amino-2-phenylethanol (0.80g, 5.841mmol) in dry THF (5mL) was then introduced by the dropwise addition over a period of 0.5h under an argon atmosphere at the same temperature. After the addition was completed, the mixture was allowed to the warm to room temperature and stirred for an appropriate time (monitored by TLC). When the reaction was completed, the THF was removed under reduced pressure. Water (10mL) was then added. The mixture was extracted with CHCl3 (2×10mL) and dried over anhydrous Na2SO4. Amide 3 was prepared as described above for 1 starting from 3-hydroxy-2-naphthoic acid (1.00g, 5.31mmol), dry THF (5mL), N-(3-dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (EDCI) (1.53g, 7.965mmol), HOBt (0.83g, 5.416mmol) and <strong>[78603-95-9](2S)-(-)-2-amino-3-methyl-1,1-diphenylbutane-1-ol</strong> (1.49g, 5.84mmol). The crude product was purified by column chromatography through silica gel, eluted with 20:1 EtOAc:MeOH solvent mixture (TLC Rf=0.34), then recrystallized from EtOAc:Hexane (3:1) mixture to give amide 3 as a yellow solid (1.51g, 67%) yield. Mp: 173-176C, [alpha]D20=-21.8 (c 1, CHCl3), IR (KBr, numax): 3350, 3057, 3030, 2960, 1648, 1616, 1520, 1447, 1305, 1226, 1172, 1061, 746, 700cm-1, 1H NMR (DMSO-d6): delta (ppm) 0.84 (d, J=6.8Hz, 3H, -CH3), 1.02 (d, J=6.8Hz, 3H, -CH3), 1.83-1.89 (m, 1H, -NHCH-), 5.22 (dd, J=1.8 and 10.0Hz, 1H, CH(i-Pro)), 6.04 (s, 1H, OH), 7.05-7.62 (m, 13H, Ar-H), 7.71 (d, J=8.2Hz, 1H, Ar-H), 7.86 (d, J=8.2Hz, 1H, Ar-H), 8.31 (s, 1H, Ar-H), 8.62 (d, J=10.0Hz, 1H, NH), 11.37 (s, 1H, Ar-OH). 13C NMR (DMSO-d6): delta (ppm) 18.59 (-CH3), 23.51 (-CH3), 29.30 (CHNH), 58.51 (CH(i-Pro)), 81.51 (-C-OH), 110.86 (Ar-C), 121.47 (Ar-C), 124.12 (Ar-C), 125.82 (Ar-C), 126.12 (Ar-C), 126.22 (Ar-C), 126.68 (Ar-C), 126.75 (Ar-C), 127.20 (Ar-C), 128.18 (Ar-C), 128.46 (Ar-C), 128.55 (Ar-C), 129.12 (Ar-C), 130.99 (Ar-C), 136.05 (Ar-C), 146.88 (Ar-C), 147.88 (Ar-C), 154.30 (Ar-C-OH), 166.81 (C=O). Anal. Calcd for C28H27NO3 (Mw: 425g/mol): C, 79.05; H, 6.35; N, 3.29. Found: C, 79.10; H, 6.40; N, 3.45 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at -15 - 20℃; Inert atmosphere; | 2.1 3-Hydroxy-N-[(1R,2S)-cis-2-hydroxy-2,3-dihydro-1H-inden-1-yl]naphthalene-2-carboxamide 7 General procedure: 3-Hydroxy-2-naphthoic acid (1.0g, 5.31mmol) was dissolved in dry THF (10mL). The mixture was cooled to -15°C, then N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI) (1.53g, 7.965mmol), and HOBt (0.83g, 5.416mmol) were added. A solution of (2S)-2-amino-2-phenylethanol (0.80g, 5.841mmol) in dry THF (5mL) was then introduced by the dropwise addition over a period of 0.5h under an argon atmosphere at the same temperature. After the addition was completed, the mixture was allowed to the warm to room temperature and stirred for an appropriate time (monitored by TLC). When the reaction was completed, the THF was removed under reduced pressure. Water (10mL) was then added. The mixture was extracted with CHCl3 (2×10mL) and dried over anhydrous Na2SO4. Amide 7 was prepared as described above for 1 starting from 3-hydroxy-2-naphthoic acid (1.00g, 5.31mmol), dry THF (5mL), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI) (1.52g, 7.96mmol), HOBt (0.83g, 5.42mmol) and (1R,2S)-(+)-cis-1-amino-2-indanol (0.87g, 5.84mmol). The crude product was recrystallized from toluene:ethyl acetate (1/1) mixture to give amide 7 as a yellow solid (1.2g, 73%) yield. Mp: 175.7-178.8°C, [α]D20=+63.0° (c 1, CH3CN). IR (KBr,νmax): 3494, 3331, 3052, 2956, 1645, 1621, 1596, 1401, 1237, 1181, 1086, 1073, 870, 745, 649cm-1, 1H NMR (DMSO-d6): δ (ppm) A part of AB spin system: 2.90 (d, J=16.4, 1H, CHBHA), B part of AB spin system: 3.15 (dd, J=4.8 and 16.4Hz, 1H, CHBHA), 4.56-4.59 (m, 1H, -CH-OH), 5.36 (d, J=4.4Hz, 1H, OH), 5.51 (q, J=5.2Hz, 1H, -NHCH-) 7.18-7.37 (m, 6H, Ar-H), 7.49-7.52 (m, 1H, Ar-H), 7.75 (d, J=8.3Hz, 1H, Ar-H), 7.92 (d, J=8.2Hz, 1H, Ar-H), 8.73 (s, 1H, Ar-H), 9.24 (d, J=8.2Hz, 1H, NH),11.62 (s, 1H, Ar-OH). 13C NMR (DMSO-d6): δ (ppm) 40.41 (-CH2- from DEPT 135 spect.), 57.82 (-CNH-), 72.43 (-COH), 110.98 (Ar-C), 120.67 (Ar-C), 124.11 (Ar-C), 124.79 (Ar-C), 125.40 (Ar-C), 126.10 (Ar-C), 126.88 (Ar-C), 127.43 (Ar-C), 127.87 (Ar-C), 128.56 (Ar-C), 129.35 (Ar-C), 132.03 (Ar-C), 136.27 (Ar-C), 141.29 (Ar-C), 142.70 (Ar-C), 154.54 (Ar-C-OH), 166.58 (C=O). Anal. Calcd for C20H17NO3 (Mw: 319g/mol): C, 75.24; H, 5.33; N, 4.39. Found: C, 75.23; H, 5.31; N, 4.43 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 10h;Cooling with ice; | Reaction flask was added 9.0 g (48. Ommol) 3-hydroxy-2-naphthoic acid, 8.3 g (60mmol) of anhydrous potassium carbonate and 30 ml of DMF dry, stirred, ice-bath cooling, 7 . 5 g (52. 5mmol) of methyl iodide was slowly added dropwise to the reaction flask And heated to 90 C for 6 hours. The reaction mixture was poured into water, extracted with methylene chloride, washed three times with a saturated sodium chloride solution, the organic layer was dried over anhydrous sodium sulfate, and evaporated to dryness to give a yellow solid 8.5 g, yield 95% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
S1. Diazotization reactionThe diazotization reaction vessel was charged with 300 ml of water, 30 g of 3-chloro-4-methylaniline-6-sulphonic acid, and 30 g of aqueous ammonia, which was stirred at 28C.Mix transparent, pH=8.2. In 20 minutes, 20 g of hydrochloric acid was added to control the acidification and stirring. Cooling to 0C with ice and adding at 25 minutesSodium nitrite 15g diazotization reaction, potassium iodide test paper micro-blue, stirring for 30 minutes. Diazotized solution I;S2. Coupling reactionAdd 200ml of water to the dissolving vessel of the coupling component, 30CAdd fire alkali35g,35g of 2-hydroxy-3-naphthoic acid, the sugar molecule obtained in the method of Example 1 was coupled to a diketopyrrolopyrrole compound 4g, stirred and dissolved to give a coupling solution II;The diazotization solution I was added to the 25C coupling solution II over 30 minutes to produce a red paste;S3. Post-processingStirred red slurry for 1 hour, pH=9.4; warmed to 43C,During this process, the permeable circle was continuously detected with filter paper until the osmosis circle disappeared. Add rosin solution,Stir for 30 minutes and add 3 g of anionic surfactant alkyl glyceryl ether sulfonate.After stirring for 10 minutes, the temperature was raised to 55C, and the barium chloride solution was added over 20 minutes and stirred for 30 minutes. Control 1C/min, heat up to 85C,After confirming the laking, it was stirred for 15 minutes. Add aluminum sulfate solution, stir for 15 minutes, add water to filter below 70 C. Filter cake passesThe moisture was removed by drying to obtain PR48:1 red pigment for 1 easily dispersible plastic.Preparation of rosin solution: Heat 500 ml of water to 100C, add 30 g of special rosin, stir for 60 minutes to completeThe solution was transparent and cooled to 50-55C to obtain a rosin solution.Barium chlorideSolution preparation: Heat 200ml of water to 40C, add 50g of antimony chloride, and dissolve it to obtain lanthanum chloride solution.liquid.Preparation of aluminum sulfate solution: Heat 100ml of water to 40C, add 16g of aluminum sulfate, and dissolve it to obtain aluminum sulfate solution.liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: bromine / acetic acid / 3 h / Cooling with ice; Reflux 2: hydrogenchloride / water; acetic acid / 3 h / Reflux 3: sulfuric acid / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23.3 g | A magnetic stirrer was set in a 200 mL beaker, to which 11.2 g of 4-aminotoluene sulfonic acid,120 g of deionized water and 13.4 g of concentrated NH4OH. The resulting mixture was stirred to dissolve the contents and then placed in an ice bath. Cool to 0 C. and add 18 mL of 23% sodium nitrite. Thereafter, a magnetic stirrer and an ice bath were placed in a 500 mL 3-neck round bottom flask, and 16.3 g of concentrated HCl and 110 g of ice / water were added thereto. While stirring, the aminotoluene sulfonic acid solution was slowly added to the HCl solution in the round bottom flask. The temperature was kept below 0 C. The contents are stirred at 0 C. or less for 2 hours after which the mixture turns black Starch-I paper, which indicates that a diazonium salt solution is formed and is ready to be coupled. Next, the coupling agent solution was added to a 1 L beaker equipped with a magnetic stirrer by adding 12.3 g of 3-hydroxy-2-naphthoic acid, 400 mL of deionized water, 30 g of concentrated NH 4 OH or 14 g of Na 2 CO 3 . The contents were dissolved and prepared for coupling. While stirring, the diazonium salt solution was slowly poured into the above coupling agent solution. The color quickly turned red. The contents had high viscosity and filtration was slow. 1 L of water was added to the reaction product and transferred to 2 1 L bottles. The reaction product contains 23.3 g of "real" product (Pigment Red 57) in 1.5 L of water / salt solution. Thereafter, the laking of the dye to the polymer (ie, stoichiometry / calculation) was based on 23.3 g of the actual dye. |
Tags: 92-70-6 synthesis path| 92-70-6 SDS| 92-70-6 COA| 92-70-6 purity| 92-70-6 application| 92-70-6 NMR| 92-70-6 COA| 92-70-6 structure
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