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[ CAS No. 27237-21-4 ]

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Chemical Structure| 27237-21-4
Chemical Structure| 27237-21-4
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Product Details of [ 27237-21-4 ]

CAS No. :27237-21-4 MDL No. :MFCD00690134
Formula : C13H9NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :259.21 g/mol Pubchem ID :-
Synonyms :

Safety of [ 27237-21-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 27237-21-4 ]

  • Downstream synthetic route of [ 27237-21-4 ]

[ 27237-21-4 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 2303-25-5 ]
  • [ 27237-21-4 ]
YieldReaction ConditionsOperation in experiment
93% With pyridine; potassium permanganate; sodium hydroxide In water at 100℃; for 10.5h; Reflux;
With chromium(VI) oxide; acetic acid
YieldReaction ConditionsOperation in experiment
95% 14.2 Step 2. To a vigorously stirred mixture of4-(3-ethoxycarbonylphenoxy)-1-nitrobenzene (5.14 g, 17.9 mmol) in a 3:1 THF/water solution (75 mL) was added a solution LiOH&Circlesolid;H2O (1.50 g, 35.8 mmol) in water (36 mL). The resulting mixture was heated at 50° C. overnight, then cooled to room temp., concentrated under reduced pressure, and adjusted to pH 2 with a 1M HCl solution. The resulting bright yellow solids were removed by filtration and washed with hexane to give 4-(3-carboxyphenoxy)-1-nitrobenzene (4.40 g, 95%).
/BRN= 2988590/;
p-Chlornitrobenzol, m-Hydroxybenzoesaeure;
  • 3
  • [ 27237-21-4 ]
  • [ 74-89-5 ]
  • [ 71708-64-0 ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dichloromethane at 20℃; for 72h; A.A13.3 Step 3. Synthesis of 4-(3-(N-methylcarbamoyl)phenoxy)-1-nitrobenzene A mixture of 4-(3-carboxyphenoxy)-1-nitrobenzene (3.72 g, 14.4 mmol), EDCI.HCl (3.63 g, 18.6 mmol), N-methylmorpholine (1.6 mL, 14.5 mmol) and methylamine (2.0 M in THF; 8 mL, 16 mmol) in CH2Cl2 (45 mL) was stirred at room temp. for 3 d, then concentrated under reduced pressure. The residue was dissolved in EtOAc (50 mL) and the resulting mixture was extracted with a 1M HCl solution (50 mL). The aqueous layer was back-extracted with EtOAc (2*50 mL). The combined organic phases were washed with a saturated NaCl solution (50 mL), dried (Na2SO4), and concentrated under reduced pressure to give 4-(3-(N-methylcarbamoyl)phenoxy)-1-nitrobenzene as an oil (1.89 g).
  • 4
  • [ 27237-21-4 ]
  • [ 54579-63-4 ]
YieldReaction ConditionsOperation in experiment
48% In methanol A11. Synthesis of 4-(3-Carboxyphenoxy)aniline A slurry of 4-(3-carboxyphenoxy)-1-nitrobenzene (5.38 g, 20.7 mmol) and 10% Pd/C (0.50 g) in MeOH (120 mL) was stirred under an H2 atmosphere (balloon) for 2 d. The resulting mixture was filtered through a pad of Celite, then concentrated under reduced pressure to afford 4-(3-carboxyphenoxy)aniline as a brown solid (2.26 g, 48%): TLC (10% MeOH/90% CH2Cl2) Rf 0.44 (streaking).
48% In methanol Synthesis of 4-(3-Carboxyphenoxy)aniline Synthesis of 4-(3-Carboxyphenoxy)aniline A slurry of 4-(3-carboxyphenoxy)-1-nitrobenzene (5.38 g, 20.7 mmol) and 10% Pd/C (0.50 g) in MeOH (120 mL) was stirred under an H2 atmosphere (balloon) for 2 d. The resulting mixture was filtered through a pad of Celite, then concentrated under reduced pressure to afford 4-(3-carboxyphenoxy)aniline as a brown solid (2.26 g, 48%): TLC (10% MeOH/90% CH2Cl2) Rf 0.44 (streaking).
48% In methanol 11 Step 1. A slurry of 4-(3-carboxyphenoxy)-1-nitrobenzene (5.38 g, 20.7 mmol) and 10% Pd/C (0.50 g) in MeOH (120 mL) was stirred under an H2 atmosphere (balloon) for 2 d. The resulting mixture was filtered through a pad of Celite, then concentrated under reduced pressure to afford 4-(3-carboxyphenoxy)aniline as a brown solid (2.26 g, 48%): TLC (10% MeOH/90% CH2Cl2) Rf 0.44 (streaking).
48% With hydrogen In methanol for 48h; A.A11 Synthesis of 4-(3-Carboxyphenoxy)aniline. Synthesis of 4-(3-Carboxyphenoxy)aniline. A slurry of 4-(3-carboxyphenoxy)-1-nitrobenzene (5.38 g, 20.7 mmol) and 10% Pd/C (0.50 g) in MeOH (120 mL) was stirred under an H2 atmosphere (balloon) for 2 d. The resulting mixture was filtered through a pad of Celite, then concentrated under reduced pressure to afford 4-(3-carboxyphenoxy)aniline as a brown solid (2.26 g, 48%): TLC (10% MeOH/90% CH2Cl2) Rf 0.44 (streaking).

  • 5
  • [ 284462-55-1 ]
  • [ 27237-21-4 ]
YieldReaction ConditionsOperation in experiment
95% In tetrahydrofuran; water 2 Step 2. Step 2. Synthesis of 4-(3-carboxyphenoxy)-1-nitrobenzene To a vigorously stirred mixture of 4-(3-ethoxycarbonylphenoxy)-1-nitrobenzene (5.14 g, 17.9 mmol) in a 3:1 THF/water solution (75 mL) was added a solution LiOH.H2O (1.50 g, 35.8 mmol) in water (36 mL). The resulting mixture was heated at 50° C. overnight, then cooled to room temp., concentrated under reduced pressure, and adjusted to pH 2 with a 1M HCl solution. The resulting bright yellow solids were removed by filtration and washed with hexane to give 4-(3-carboxyphenoxy)-1-nitrobenzene (4.40 g, 95%).
95% With LiOH-H2O In tetrahydrofuran; water 13.2 Step 2. Step 2. Synthesis of 4-(3-carboxyphenoxy)-1-nitrobenzene To a vigorously stirred mixture of 4-(3-ethoxycarbonylphenoxy)-1-nitrobenzene (5.14 g, 17.9 mmol) in a 3:1 THF/water solution (75 mL) was added a solution LiOH-H2O (1.50 g, 35.8 mmol) in water (36 mL). The resulting mixture was heated at 50° C. overnight, then cooled to room temp., concentrated under reduced pressure, and adjusted to pH 2 with a 1M HCl solution. The resulting bright yellow solids were removed by filtration and washed with hexane to give 4-(3-carboxyphenoxy)-1-nitrobenzene (4.40 g, 95%).
95% Stage #1: ethyl 3-(4'-nitrophenoxy)benzoate With lithium hydroxide; water In tetrahydrofuran at 50℃; Stage #2: With hydrogenchloride A.A13.2 Step 2. Synthesis of 4-(3-carboxyphenoxy)-1-nitrobenzene To a vigorously stirred mixture of 4-(3-ethoxycarbonylphenoxy)-1-nitrobenzene (5.14 g, 17.9 mmol) in a 3:1 THF/water solution (75 mL) was added a solution LiOH-H2O (1.50 g, 35.8 mmol) in water (36 mL). The resulting mixture was heated at 50° C. overnight, then cooled to room temp., concentrated under reduced pressure, and adjusted to pH 2 with a 1M HCl solution. The resulting bright yellow solids were removed by filtration and washed with hexane to give 4-(3-carboxyphenoxy)-1-nitrobenzene (4.40 g, 95%).
4.6 g Stage #1: ethyl 3-(4'-nitrophenoxy)benzoate With lithium hydroxide monohydrate In tetrahydrofuran; water at 50℃; for 4h; Stage #2: With hydrogenchloride In water

YieldReaction ConditionsOperation in experiment
Syntheses of Exemplified Compounds (see Tables for Compound Characterization) According to Method C1a, 4-chloro-3-(trifluoromethyl)phenyl isocyanate was reacted with 4-(4-acetylphenoxy)aniline to afford the urea. Entry 61: 4-(3-Carboxyphenoxy)-1-nitrobenzene was synthesised according to Method A13, Step 2. 4-(3-Carboxyphenoxy)-1-nitrobenzene was coupled with 4-(2-aminoethyl)morpholine according to Method A13, Step 3 to give 4-(3-(N-(2-morpholinylethyl)carbamoyl)phenoxy)-1-nitrobenzene.
(See Tables for Compound Characterization) According to Method C1a, 4-chloro-3-(trifluoromethyl)phenyl isocyanate was reacted with 4-(4-acetylphenoxy)aniline to afford the urea. Entry 61: 4-(3-Carboxyphenoxy)-1-nitrobenzene was synthesised according to Method A13, Step 2. 4-(3-Carboxyphenoxy)-1-nitrobenzene was coupled with 4-(2-aminoethyl)morpholine according to Method A13, Step 3 to give 4-(3-(N-(2-morpholinylethyl)carbamoyl)phenoxy)-1-nitrobenzene.
  • 7
  • [ 27237-21-4 ]
  • [ 71708-64-0 ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; methylamine In tetrahydrofuran; dichloromethane; ethyl acetate 3 Step 3. Step 3. Synthesis of 4-(3-(N-methylcarbamoyl)phenoxy)-1-nitrobenzene A mixture of 4-(3-carboxyphenoxy)-1-nitrobenzene (3.72 g, 14.4 mmol), EDCI.HCl (3.63 g, 18.6 mmol), N-methylmorpholine (1.6 mL, 14.5 mmol) and methylamine (2.0 M in THF; 8 mL, 16 mmol) in CH2Cl2 (45 mL) was stirred at room temp. for 3 d, then concentrated under reduced pressure. The residue was dissolved in EtOAc (50 mL) and the resulting mixture was extracted with a 1M HCl solution (50 mL). The aqueous layer was back-extracted with EtOAc (2*50 mL). The combined organic phases were washed with a saturated NaCl solution (50 mL), dried (Na2SO4), and concentrated under reduced pressure to give 4-(3-(N-methylcarbamoyl)phenoxy)-1-nitrobenzene as an oil (1.89 g).
With 4-methyl-morpholine; methylamine In tetrahydrofuran; dichloromethane; ethyl acetate 13.3 Step 3. Step 3. Synthesis of 4-(3-(N-methylcarbamoyl)phenoxy)-1-nitrobenzene A mixture of 4-(3-carboxyphenoxy)-1-nitrobenzene (3.72 g, 14.4 mmol), EDCI.HCl (3.63 g, 18.6 mmol), N-methylmorpholine (1.6 mL, 14.5 mmol) and methylamine (2.0 M in THF; 8 mL, 16 mmol) in CH2Cl2 (45 mL) was stirred at room temp. for 3 d, then concentrated under reduced pressure. The residue was dissolved in EtOAc (50 mL) and the resulting mixture was extracted with a 1M HCl solution (50 mL). The aqueous layer was back-extracted with EtOAc (2*50 mL). The combined organic phases were washed with a saturated NaCl solution (50 mL), dried (Na2SO4), and concentrated under reduced pressure to give 4-(3-(N-methylcarbamoyl)phenoxy)-1-nitrobenzene as an oil (1.89 g).
With 4-methyl-morpholine; methylamine In tetrahydrofuran; dichloromethane; ethyl acetate 3 Step 3. Step 3. Synthesis of 4-(3-(N-methylcarbamoyl)phenoxy)-1-nitrobenzene A mixture of 4-(3-carboxyphenoxy)-1-nitrobenzene (3.72 g, 14.4 mmol), EDCIHCl (3.63 g, 18.6 mmol), N-methylmorpholine (1.6 mL, 14.5 mmol) and methylamine (2.0M in THF; 8 mL, 16 nunol) in CH2Cl2 (45 mL) was stirred at room temp. for 3 d, then concentrated under reduced pressure. The residue was dissolved in EtOAc (50 mL) and the resulting mixture was extracted with a 1M HCl solution (50 mL). The aqueous layer was back-extracted with EtOAc (2*50 mL). The combined organic phases were washed with a saturated NaCl solution (50 mL), dried (Na2SO4), and concentrated under reduced pressure to give 4-(3-(N-methylcarbamoyl)phenoxy)-1-nitrobenzene as an oil (1.89 g).
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 50 °C 2: triethylamine / dichloromethane / 20 °C

YieldReaction ConditionsOperation in experiment
(See Tables for Compound Characterization) According to Method C1a, 4-chloro-3-(trifluoromethyl)phenyl isocyanate was reacted with 4-(4-acetylphenoxy)aniline afford the urea. Entry 61: 4-(3-Carboxyphenoxy)-1-nitrobenzene was synthesised according to Method A13, Step 2. 4-(3-Carboxyphenoxy)-1-nitrobenzene was coupled with 4-(2-aminoethyl)morpholine according to Method A13, Step 3 to give 4-(3-(N-(2-morpholinylethyl) carbamoyl)phenoxy)-1-nitrobenzene.
  • 9
  • LiOHH2O [ No CAS ]
  • [ 284462-55-1 ]
  • [ 27237-21-4 ]
YieldReaction ConditionsOperation in experiment
95% In tetrahydrofuran; water 2 Step 2. Step 2. Synthesis of 4-(3-carboxyphenoxy)-1-nitrobenzene To a vigorously stirred mixture of 4-(3-ethoxycarbonylphenoxy)-1-nitrobenzene (5.14 g, 17.9 mmol) in a 3:1 THF/water solution (75 mL) was added a solution LiOHH2O (1.50 g, 35.8 mmol) in water (36 mL). The resulting mixture was heated at 50° C. overnight, then cooled to room temp., concentrated under reduced pressure, and adjusted to pH 2 with a 1M HCl solution. The resulting bright yellow solids were removed by filtration and washed with hexane to give 4-(3-carboxyphenoxy)-1-nitrobenzene (4.40 g, 95%).
  • 10
  • EDCI·HCl [ No CAS ]
  • [ 27237-21-4 ]
  • 4-(3-(N-methylearbamoyl)phenoxy)-1-nitrobenzene [ No CAS ]
  • [ 71708-64-0 ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; methylamine In tetrahydrofuran; dichloromethane; ethyl acetate 3 Step 3. Step 3. Synthesis of 4-(3-(N-methylearbamoyl)phenoxy)-1-nitrobenzene A mixture of 4-(3-carboxyphenoxy)-1-nitrobenzene (3.72 g, 14.4 mmol), EDCI·HCl (3.63 g, 18.6 mmol), N-methylmorpholine (1.6 mL, 14.5 mmol) and methylamine (2.0 M in THF; 8 mL, 16 mmol) in CH2Cl2 (45 mL) was stirred at room temp. for 3 d, then concentrated under reduced pressure. The residue was dissolved in EtOAc (50 mL) and the resulting mixture was extracted with a 1M HCl solution (50 mL). The aqueous layer was back-extracted with EtOAc (2*50 mL). The combined organic phases were washed with a saturated NaCl solution (50 mL), dried (Na2SO4), and concentrated under reduced pressure to give 4-(3-(N-methylcarbamoyl)phenoxy)-1-nitrobenzene as an oil (1.89 g).
  • 11
  • LiOH·H2O [ No CAS ]
  • [ 284462-55-1 ]
  • [ 27237-21-4 ]
YieldReaction ConditionsOperation in experiment
95% In tetrahydrofuran; water 2 Step 2. Step 2. Synthesis of 4-(3-carboxyphenoxy)-1-nitrobenzene To a vigorously stirred mixture of 4-(3-ethoxycarbonylphenoxy)-1-nitrobenzene (5.14 g, 17.9 mmol) in a 3:1 THF/water solution (75 mL) was added a solution LiOH·H2O (1.50 g, 35.8 mmol) in water (36 mL). The resulting mixture was heated at 50° C. overnight, then cooled to room temp., concentrated under reduced pressure, and adjusted to pH 2 with a 1M HCl solution. The resulting bright yellow solids were removed by filtration and washed with hexane to give 4-(3-carboxyphenoxy)-1-nitrobenzene (4.40 g, 95%).
  • 12
  • [ 99-06-9 ]
  • [ 100-00-5 ]
  • [ 27237-21-4 ]
YieldReaction ConditionsOperation in experiment
94% With sodium hydroxide; ammonia In water 25 EXAMPLE 25 EXAMPLE 25 88.5 g (0.635 moles) of 3-hydroxy benzoic acid (99% pure), 100 g of p-nitrochlorebenzene, and 51,4 g sodium hydroxide (98.8% pure) were introduced into an autoclave. After removal of the air by evacuation, 150 g of ammonia were pumped into the autoclave. The mixture was stirred for 10 hours at 80° C. The initial pressure of 37 bars dropped to 34 bars during the reaction. After cooling and removal of the ammonia, the reaction product was dissolved in 800 ml of water. By acidification with hydrochloric acid the crude 3-(4'-nitrophenoxy)-benzoic acid was precipitated. Purity: 97.3%; the product could be purified by recristallization. Yield: 94%; m.p. 188° C.
  • 13
  • [ 99-06-9 ]
  • [ 350-46-9 ]
  • [ 27237-21-4 ]
YieldReaction ConditionsOperation in experiment
98% With potassium carbonate In dimethyl sulfoxide at 130℃; for 12h; 1 Synthesis Example 1 3-(4-nitrophenoxy)benzoic acid 7.52 ml of fluoro-4-nitrobenzene (70.8 mmol) and 9.79 g of 3-hydroxybenzoic acid (70.8 mmol) were dissolved in 150 ml of DMSO at room temperature, 21 g of potassium carbonate (151.9 mmol) was added thereto, heated to 130° C. and then reacted for 12 hours. The reactant solution was poured into excess water, neutralized with hydrochloric acid, filtered, and dried to yield a product having Formula 25 as a white powder (18.7 g, Yield 98%). 1H NMR (300 MHz, CDCl3) analytical results of the product were as follows: 1H NMR (300 MHz, CDCl3): [ppm] 7.03 (d, 2H), 7.33 (d, 1H), 7.54 (t, 1H), 7.80 (s, 1H), 7.98 (d, 1H), 8.22 (d, 2H), 12.70 (s, 1H)
  • 14
  • [ 64-17-5 ]
  • [ 27237-21-4 ]
  • [ 284462-55-1 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride In water at 110℃; for 12h; 2 Synthesis Example 2; ethyl3-(4-nitrophenoxy)benzoate; 18 g of 3-(4-nitrophenoxy)benzoic acid (69.4 mmol) prepared in Synthesis Example 1 was dissolved in 120 ml of ethanol, 35 ml of hydrochloric acid (10N) was added thereto, heated to 110° C. and then reacted for 12 hours. The reactant solution was poured into excess water, neutralized with a 1N aqueous solution of sodium chloride, filtered, and dried with magnesium sulfate, followed by removing ethylacetate, to yield a tacky product having Formula 26 (19 g (65 mmol), Yield 95%). 1H NMR (300 MHz, CDCl3) analytical results of the product were as follows:1H NMR (300 MHz, CDCl3): [ppm] 1.28 (s, 3H), 4.30 (t, 2H), 7.20 (d, 2H), 7.35 (d, 1H), 7.73 (s, 1H), 7.82 (t, 1H), 7.78 (d, 1H), 8.22 (d, 2H).
  • 15
  • [ 27237-21-4 ]
  • 3-(4-nitro-phenoxy)-benzoic acid hydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 12 h / 110 °C 2: hydrazine hydrate / ethanol / 24 h / Reflux
  • 16
  • [ 27237-21-4 ]
  • [ 1253119-88-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogenchloride / water / 12 h / 110 °C 2: hydrazine hydrate / ethanol / 24 h / Reflux 3: tetrahydrofuran / 12 h / 20 °C 4: trichlorophosphate / 12 h / 90 °C
  • 17
  • [ 27237-21-4 ]
  • [ 1253119-89-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogenchloride / water / 12 h / 110 °C 2: hydrazine hydrate / ethanol / 24 h / Reflux 3: tetrahydrofuran / 12 h / 20 °C 4: trichlorophosphate / 12 h / 90 °C 5: boron tribromide / dichloromethane / -78 - 0 °C
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