4-Amino-3-chlorophenol hydrochloride
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4-Amino-3-chlorophenol hydrochloride
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CAS No:
52671-64-4
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Formula:
C6H6ClNO.ClH
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Chemical Name:
4-Amino-3-chlorophenol hydrochloride
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Synonyms:
Phenol,4-amino-3-chloro-,hydrochloride (1:1);Phenol,4-amino-3-chloro-,hydrochloride;3-Chloro-4-aminophenol hydrochloride;2-Chloro-4-hydroxyaniline hydrochloride;4-Amino-3-chlorophenol hydrochloride
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CAS No:
Characteristics
46.2
3.01100
GREY TO BROWN POWDER, CRYSTALS, CRYSTALLINE POWDER AND/OR CHUNKS
1.406g/cm3
234 °C
314ºC at 760 mmHg
143.7ºC
Safety Information
NONH for all modes of transport
3
36/37/38
26-36
Xi
P261-P305 + P351 + P338
H315-H319-H335
4-Amino-3-chlorophenol hydrochloride Use and Manufacturing
A solution of 4-Amino-3-chlorophenol-HCl (990 g) was added to N, N-dimethylacetamide (6.6 L). Potassium t-butoxide (1452 g) was added thereto at 0°C, and the mixture was stirred at 20°C for 30 min. 4-Chloro-6, 7-dimethoxyquinoline (825 g) was added to the reaction solution, and the mixture was then stirred at 115°C for 5 hr. The reaction solution was cooled to room temperature, water (8.3 L) and methanol (8.3 L) were then added thereto, and the mixture was stirred for 2 hr. The resultant precipitate was collected by filtration, and the filtered product was slurried in water (8.3 L) for washing. The slurry was filtered, and the filtered product was then dried under the reduced pressure to give 4-[(4-amino-3-chlorophenol)oxy]-6, 7-dimethoxyquinoline (852 g, yield 69.9percent). 1H-NMR (400 MHz, DMSO-d6/ppm); delta 3.92 (s, 3H), 3.93 (s, 3H), 5.41 (s, 2H), 6.41 (d, 1H), 6.89 (d, 1H), 6.98 (dd, 1H), 7.19 (d, 1H), 7.36 (s, 1H), 7.48 (s, 1H), 8.43 (d, 1H)Production 2-Chloro-4-[(6, 7-dimethoxy-4-quinolyl)oxy]aniline Sodium hydride (60 wtpercent, 0.72 g) was added to dimethyl sulfoxide (10 ml). The mixture was stirred at 50°C for 30 min and was then cooled to room temperature. 4-Chloro-7-methoxyquinolin-6-amide (10g) andK2003 (3.89 g, 28.15 mmol) and ethyl iodide (0.99 mL, 12.40 mmol) were added to a suspension of Example 4 4-(4-amino-3-chlorophenoxy)-7-methoxyquinoline-6-carboxamide'monohydrate (0153) (0154) A mixture of Potassium hydroxide (41.50 g, 3.5 eq) was added to a three-neck reaction flask containing 500 ml of dimethyl sulfoxide containing 10% water.SM2 (57.00 g, 1.5 eq) was added in one portion at room temperature. After the addition is completed, the mixture is stirred at room temperature for about 3 minutes.50.00 g of the compound of formula 1 was added in one portion, the temperature was raised to 110 C, and the reaction was kept for 2 h.Acetone was added while hot: water = 1:10 (1.5 L), and the mixture was decanted to room temperature, and the filter cake was collected by filtration, and dried under vacuum at 45 C overnight.Collecting 68g of reddish brown solid formula 2 compound, The purity of the reaction solution was 97.81%.The crude product had a purity of 98.51% and a yield of 94.44%.9.89 g of 4-chloro-7-methoxyquinoline-6-carboxamide compound of formula-7 (100 g) was added the mixture of 4-amino-3-chloro-phenol hydrochloride (102.7 g), aqueous potassium hydroxide solution (71.13 g of potassium hydroxide in 75 ml of water) and dimethyl sulfoxide (900 ml) at 25-30C. Heated the reaction mixture to 75-80C and stirred for 8 hours at the same temperature. The reaction mixture was cooled to 50-55C, aqueous acetone was added to reaction mixture and stirred for 10 minutes. The reaction mixture was cooled to 0-5C and stirred for 1 hour at same temperature. Filter the precipitated solid, washed with aqueous acetone and dried. N-Methyl-2-pyrrolidone was added to the above obtained solid at 25-30C. Heated the mixture to 75-80C and stirred for 15 minutes at the same temperature. The mixture was cooled to 50-55C, ethyl acetate was added to the mixture and stirred for 5 minutes. Cool the mixture to 25-30C and stirred for 2 hours at same temperature. Filtered the precipitated solid and washed with ethyl acetate. The obtained solid was slurried in acetone, filtered and washed with acetone, dried to get the title compound. Yield: 101 g, Purity by HPLC: 99.96%, MR: 2l5-225C.
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4-Amino-3-chlorophenol hydrochloride
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