[ CAS No. 4694-91-1 ] {[proInfo.proName]}

Name: 4694-91-1|6-Nitrobenzo[d]oxazol-2(3H)-one|98%
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CAS No. :	4694-91-1	MDL No. :	MFCD00463755
Formula :	C₇H₄N₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JGYJZHYTADCWIK-UHFFFAOYSA-N
M.W :	180.12	Pubchem ID :	78419
Synonyms :

Safety of [ 4694-91-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 4694-91-1 ]

* 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 [ 4694-91-1 ]
Downstream synthetic route of [ 4694-91-1 ]

[ 4694-91-1 ] Synthesis Path-Upstream 1~1

1
[ 4694-91-1 ]
[ 121-88-0 ]

Yield	Reaction Conditions	Operation in experiment
84.4%	at 95℃; for 2 h;	Step two obtained 27.3g of 6- nitrobenzoxazolone was added to a 250ml three-necked round-bottomed flask, followed by addition of 100ml 10percent mass fraction sodium hydroxide solution. Stirred and heated. Slowly warmed to 95 deg. C, and maintain temperature for 2 hours. cooled to room temperature, to reflect the end, the mixture was adjusted with hydrochloric acid PH = 6, then washed, suction filtration and dried, to give 5-nitro-2- aminophenol 20.3g of product, yield was 84.4percent .

Reference： [1] Patent: CN105669477, 2016, A, . Location in patent: Paragraph 0025

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Yield	Reaction Conditions	Operation in experiment
94.4%	With nitric acid at 35℃; for 2h;	1.2 Step two: The step one obtained 27.2g benzooxazolone ring compound and 20ml acidic imidazole ionic liquid were added together to a 250ml neck round bottom flask and thoroughly mixed. Then the pre-mixed well 10.5ml 65% mass fraction nitric acid was added dropwise to a 250ml three-necked round bottom flask. At a temperature of 35 deg.C reacted for 2 hours. Afterwards, heating was stopped, cooled to room temperature, washed, filtration, and dried to give 6-nitrobenzooxazole 34.4g, yield was 94.4%;
87%	With nitric acid at 0 - 20℃; for 4h;	46 4.1.46 6-Nitro-3H-1,3-benzoxazol-2-one (45) 70% Nitric acid (50 mL, 0.80 mol) was cooled to 0 °C and 3H-1,3-benzoxazol-2-one (5.00 g, 37 mmol) was added. The reaction mixture was stirred at rt for 4 h and then poured in ice.The resulting precipitate was collected by filtration, washed with water and dried to give a pink solid (5.80 g, 32.5 mmol, 87%). Mp > 250 °C. 1H NMR (300 MHz, DMSOd6): δ 12.41 (s, 1H), 8.20 (d, J = 2.2 Hz, 1H), 8.13 (dd, J = 8.6 Hz, J = 2.2 Hz, 1H), 7.28 (d, J = 8.6 Hz, 1H).13C NMR (300 MHz, DMSOd6): δ 154.7, 143.2, 142.5, 137.2, 121.2, 109.8, 105.8. LCMS m/z calc for [M - H]+: 179.0, found: 179.0.
87%	With nitric acid at 0 - 20℃; for 4h;	6-Nitro-3H-1,3-benzoxazol-2-one (45) Nitric acid (50 mL, 0.80 mol) was cooled to 0°C and 3H-1,3-benzoxazol-2-one (5.00 g, 37 mmol) was added. The reaction mixture was stirred at rt for 4 h and then poured in ice. The resulting precipitate was collected by filtration, washed with water and dried to give 45 asa pink solid (5.80 g, 87 %). Mp 250°C. 1H NMR (300 MHz), 5 (ppm, DMSO-d6): 12.41 (s,1H), 8.20 (d, J= 2.2 Hz, 1H), 8.13 (dd, J= 8.6 Hz, J 2.4 Hz, 1H), 7.28 (d, J 8.6 Hz,1H). 13C NMR (75 MHz), 5 (ppm, DMSO-d6): 154.7, 143.2, 142.5, 137.2, 121.2, 109.8,105.8. LCMS mlz calc for [M-H]: 179.0, found: 179.0.

79%	With nitric acid In water at 20℃; for 2.5h; Heating;
77%	With sulfuric acid; nitric acid In nitromethane at 0 - 20℃; for 3h; regioselective reaction;
72%	With nitric acid at 20 - 50℃; for 19h;	a.i i) Synthesis of 6-nitro-3H-1,3-benzoxazol-2-one 40.0 g (0.30 mol) of 2-benzoxazolinone were dissolved with stirring at room temperature in 600.0 ml (0.30 mole) of 68% nitric acid. It was then heated to 50° C. and stirred at this temperature for three hours. The reaction was stirred for a further 16 h at room temperature. After completion of the reaction, the mixture was poured into about 2.0 l of ice water, precipitated substance was filtered off, washed neutral and dried. After drying, 6-nitro-3H-1,3-benzoxazol-2-one (39.1 g, 72%) was obtained as a pale yellow solid. 1H-NMR (300 MHz, d6-DMSO): δ=7.25 (d, 1H, 4-H), 8.10 (d, 1H, 5-H), 8.17 (s, 1H, 7-H), 12.43 (br s, 1H, NH).
67.77%	With nitric acid; acetic anhydride at 0 - 5℃; for 3h;	General procedure for the synthesis of 6-nitro-2(3H)-benzoxazolone and 3-methyl-6-nitro-2(3H)-benzoxazolone compounds (2a-b) General procedure: Nitric acid (68%, 5.30 cm3, 80 mmol) cooled to 0-5°Cwas added dropwise to a solution of benzoxazolinone (10 mmol) in 20 cm3 of acetic anhydride. The mixture was stirred at 0-5°C for 3 h. The precipitate was filtered, washed with cold H2O, dried, and recrystallized from suitable solvent to afford the corresponding nitrobenzoxazolones compounds 3a (67.77%) and 3b (91%).
67%	With nitric acid; acetic anhydride at -5 - 0℃;
	With nitric acid
	With mixture of gaseous nitrogen oxides; acetic acid
	With nitric acid
	With nitric acid at 0℃; man giesst auf Eis;
	With nitric acid

Yield	Reaction Conditions	Operation in experiment
97%	With hydrogen In tetrahydrofuran; water at 20℃; for 9h;	13.b b) Synthesis of Compound 24 Compound 23 (40.00 g, 222 mmol) was suspended in THF-water (9:1) mixed solution (400 ml), 10%-palladium-carbon (8.00 g, 53% water-containing product) was added, and the mixture was stirred at room temperature for 9 hours under the hydrogen atmosphere. The reaction solution was filtered using Celite, and the residue was washed with THF-water (9:1) mixed solution (500 ml). The filtrate and the washing solution were combined, and concentrated to 96 g under reduced pressure, water (100 ml) was added, and the solid was collected by filtration. The solid was washed with water, and dried to obtain Compound 24 (32.20 g, yield 97%). 1H-NMR (DMSO-d6 / TMS) δppm: 5.01 (s, 1H), 6.35 (dd, J = 2.0, 8.2Hz, 1H), 6.50 (d, J = 2.0Hz, 1H), 6.74 (d, J = 8.2Hz, 1H), 11.03 (brs, 1H).
95%	With hydrogen In methanol; ethanol	2.2n 6-Amino-3H-benzooxazol-2-one can be synthesized by the following procedure. A solution of 6- nitro-3H-benzooxazol-2-one (7.22 mmol) in a 1:3 mixture EtOH : MeOH (24 mL) is treated with Pd (5% on carbon, 50% wet, 10% weight). The flask is charged with a hydrogen balloon and stirred overnight.The mixture is filtered over celite and the filtrate is concentrated to afford the 6-amino-benzoxazole-2- one as light brown powder (95%). 1HNMR (400 MHz, DMSO-d6) δ 11.06 (b.s,. IH), 6.74 (d, J = 8.2Hz,IH), 6.49 (d, J = 2.0Hz, IH), 6.35 (dd, J = 2.1 and 8.3Hz, IH), 4.96 (s, 2H). MS (m/z) (M+l)+ 151.1.
70%	With palladium on activated charcoal; ammonium bicarbonate In methanol for 4h; Reflux;

69%	With tin(II) chloride dihdyrate In ethanol for 3h; Reflux;
65%	With hydrogen In tetrahydrofuran for 16h;	I.5.g Synthesis of 6-Amino-3H-benzooxazol-2-one (30)5 g (26.9 mmol) 6-Nitrobenoxazol-2(3H)-on were dissolved in 100 ml THF and 1 g Pd-C-5% (containing 50.5% water) were added. The reaction was hydrogenated with H2 over 16 h. The reaction mixture was then filtered over celite and reduced in vacuo. Thereby the desired product 30 was isolated as a red-brown solid (2.6 g, 17.4 mmol, 65%).
55.39%	With palladium 10% on activated carbon; ammonium formate In methanol for 3h; Reflux;	General procedure for the synthesis of 6-amino-2(3H)-benzoxazolone and 6-amino-3-methyl-2(3H)-benzoxazolone compounds (3a-b) General procedure: To a mixture of 6-nitro-2(3H)-benzoxazolone 2a (8.1 mmol,0.145 g) or 3-methyl-6-nitro-2(3H)-benzoxazolinone 2b(8.1 mmol, 0.157 g) and 10% Pd/C (375 mg) in 30 mL of methanol was added ammonium formate (2.55 g, 40.5 mmol,5equiv), and the reaction was heated to reflux for 3 h until the reaction was complete and the starting material disappeared a sindicated by TLC analysis. The reaction mixture was allowed to cool down, filtered through Celite, and evaporated to givethe desired amines 3a (55.39%) and 3b (73.36%).
	With sodium hydroxide; sodium dithionite
	With hydrogenchloride; iron
	With hydrogenchloride; tin
	With palladium on activated charcoal; ethanol Hydrogenation;
	With hydrogenchloride; tin
	With hydrogen In acetone Ambient temperature;
	With hydrogenchloride; iron at 90℃;

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[ 4694-91-1 ] Synthesis Path-Upstream 1~1

[ 4694-91-1 ] Synthesis Path-Downstream 1~88