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Quality Control of [ 289483-81-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 289483-81-4 ]

CAS No. :	289483-81-4	MDL No. :	MFCD17779299
Formula :	C₁₀H₈N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ILKYFKTXIFABKK-UHFFFAOYSA-N
M.W :	204.18	Pubchem ID :	18752857
Synonyms :

Safety of [ 289483-81-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 289483-81-4 ]

* 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 [ 289483-81-4 ]
Downstream synthetic route of [ 289483-81-4 ]

[ 289483-81-4 ] Synthesis Path-Upstream 1~4

1
[ 289483-81-4 ]
[ 289483-82-5 ]

Yield	Reaction Conditions	Operation in experiment
89.7%	Stage #1: With pyridine; hydroxylamine hydrochloride In N,N-dimethyl-formamide at 60℃; for 0.666667 h; Stage #2: With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 0 - 60℃; for 0.5 h; Stage #3: With triethylamine In N,N-dimethyl-formamide at 60℃; for 1 h;	Reference Example 2A Synthesis of 3-cyano-4-methyl-7-nitro-1H-indole After dissolving 2.21 g (10.8 mmol) of the 3-formyl-4-methyl-7-nitro -1H-indole obtained in Reference Example 1A in 100 mL of dimethylformamide, 900 mg (13.0 mmol) of hydroxylamine hydrochloride and 1.05 mL (13.0 mmol) of pyridine were added. The mixture was heated and stirred at 60° C. for 40 minutes, and then 1,1'-carbonyldiimidazole (53.9 mmol) was added to the reaction mixture while cooling in an ice bath. The mixture was further heated and stirred at 60° C. for 30 minutes, and then 3.0 mL (21.5 mmol) of triethylamine was added to the reaction mixture, and heating and stirring were continued at the same temperature for 1 hour. To the reaction mixture was added 50 mL of ice water while cooling in an ice bath and extraction was performed with ethyl acetate. The organic layer was washed with water and brine in that order, dried over magnesium sulfate, and concentrated to dryness. A mixture of tert-butyl methyl ether and hexane was added to the residue, and the crystals were collected by filtration to give 1.95 g of the title compound (yield: 89.7percent). ¹H-NMR (DMSO-d₆) δ (ppm): 2.78 (3H, s), 7.22 (1H, d, J=8.0Hz), 8.14 (1H, d, J=8.0Hz), 8.41 (1H, s), 12.76 (1H, br s).

Reference： [1] Patent: US2007/37854, 2007, A1, . Location in patent: Page/Page column 5-6

2
[ 289483-81-4 ]
[ 530-62-1 ]
[ 289483-82-5 ]

Reference： [1] Patent: US2002/128480, 2002, A1,
[2] Patent: EP1258252, 2002, A1,
[3] Patent: US2004/18192, 2004, A1,

3
[ 289483-80-3 ]
[ 68-12-2 ]
[ 289483-81-4 ]

Yield	Reaction Conditions	Operation in experiment
95.8%	Stage #1: at 0℃; for 20.5 h; Stage #2: at 0 - 90℃; for 21 h; Stage #3: With sodium hydroxide In water; N,N-dimethyl-formamide at 0℃;	Reference Example 1A Synthesis of 3-formyl-4-methyl-7-nitro-1H-indole To 12 mL (154 mmol) of dimethylformamide was added 1.5 mL (16.1 mmol) of phosphorous oxychloride at 0° C., followed by stirring at the same temperature for 20.5 hour. To the reaction mixture was then added a solution of 2.0 g (11.4 mmol) of 4-methyl-7-nitro-1H-indole in dimethylformamide (20 mL) at 0° C., followed by heating and stirring at 90° C. for 21 hours. To the reaction mixture was added 100 mL of 1 N aqueous solution of sodium hydroxide to the reaction mixture while cooling in an ice bath, and extraction was performed with ethyl acetate. The organic layer was washed with water and brine in that order, dried over magnesium sulfate, and concentrated to dryness. A mixture of tert-butyl methyl ether and hexane was added to the residue, and the crystals were collected by filtration to give 2.23 g of the title compound (yield: 95.8percent). ¹H-NMR (DMSO-d₆) δ (ppm): 2.90 (3H, s), 7.21 (1H, d, J=8.4Hz), 8.11 (1H, d, J=8.4Hz), 8.39 (1H, s), 10.01 (1H, s), 12.71 (1H, br s).

Reference： [1] Patent: US2007/37854, 2007, A1, . Location in patent: Page/Page column 5

4
[ 289483-80-3 ]
[ 289483-81-4 ]

Reference： [1] Patent: US2002/128480, 2002, A1,
[2] Patent: EP1258252, 2002, A1,
[3] Patent: US2004/18192, 2004, A1,

[ 289483-81-4 ] Synthesis Path-Downstream 1~5

1
[ 289483-80-3 ]
[ 289483-81-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With trichlorophosphate; In N,N-dimethyl-formamide; at 0 - 90℃; for 2h;	To a stirred solution of indole Sl-1 (1.50 g, 8.52 mmol) in DMF (10 mL) at 0 C was added POCb (3.91 g, 25.57 mmol, 3.0 equiv) dropwise. After stirring at 90 C for 2 h, the reaction was quenched with NaOH (2.0 M aq., 20 mL). The resulting mixture was stirred at this temperature for lh and then diluted with EtOAc (300 mL). The combined organic phases were washed with brine (3 x 200 mL), dried over anhydrous Na2S04 and concentrated under reduced pressure to afford indolyl aldehyde Sl-2 (1.63 g, 7.99 mmol, 94% yield) as a yellow solid
	With sodium hydroxide; trichlorophosphate; In N-methyl-acetamide; hexane; tert-butyl methyl ether;	Production Example 5 3-Formyl-<strong>[289483-80-3]4-methyl-7-nitro-1H-indole</strong> To 12 ml (154 mmol) of dimethylformamide was added 1.5 ml (16.1 mmol) of phosphorus oxychloride at 0 C. in a nitrogen atmosphere followed by stirring at room temperature at the same temperature for 20.5 hours. A solution (20 ml) of 2.0 g (11.4 mmol) of the compound of Production Example 4 in dimethylformamide was added thereto at 0 C. followed by heating at 90 C. for 21 hours under stirring. To the reaction solution was added 100 ml of a 1N aqueous solution of sodium hydroxide under ice-cooling followed by extracting with ethyl acetate. The organic layer was washed with water and brine successively, dried over magnesium sulfate and concentrated to dryness. To the resulting residue was added a mixed solution of tert-butyl methyl ether and hexane and the resulting crystals were collected by filtration to give 2.23 g of the title compound. 1H-NMR(DMSO-d6) delta (ppm); 2.90(3H,s), 7.21(1H,d,J=8.4 Hz), 8.11(1H,d,J=8.4 Hz), 8.39(1H,s), 10.01(1H,s), 12.71(1H,brs).
	With sodium hydroxide; trichlorophosphate; In N-methyl-acetamide; hexane; tert-butyl methyl ether;	Production Example 5 3-Formyl-<strong>[289483-80-3]4-methyl-7-nitro-1H-indole</strong> 1.5 ml (16.1 mmol) of phosphorous oxychloride was added to 12 ml (154 mmol) of dimethylformamide at 0C in nitrogen atmosphere, followed by stirring at the same temperature for 20.5 hours. A dimethylformamide solution (20 ml) containing 2.0 g (11.4 mmol) of the compound of Production Example 4 was added thereto at 0C, followed by heating under stirring at 90C for 21 hours. 100 ml of a 1N aqueous sodium hydroxide was added to the reaction solution under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and brine, dried over magnesium sulfate and concentrated to dryness. A mixed solution of tert-butyl methyl ether and hexane was added to the residue, and the crystals were collected by filtration, to give 2.23 g of the title compound. 1H-NMR(DMSO-d6) delta (ppm): 2.90(3H, s), 7.21(1H, d, J=8.4Hz), 8.11(1H, d, J=8.4Hz), 8.39(1H, s), 10.01(1H,s), 12.71(1H,br s)

With aqueous sodium hydroxide; trichlorophosphate; In N-methyl-acetamide; hexane; tert-butyl methyl ether;

PRODUCTION EXAMPLE 5 3-Formyl-<strong>[289483-80-3]4-methyl-7-nitro-1H-indole</strong> 1.5 ml (16.1 mmol) of phosphorous oxychloride was added to 12 ml (154 mmol) of dimethylformamide at 0 C. in nitrogen atmosphere, followed by stirring at the same temperature for 20.5 hours. A dimethylformamide solution (20 ml) containing 2.0 g (11.4 mmol) of the compound of Production Example 4 was added thereto at 0 C., followed by heating under stirring at 90 C. for 21 hours. 100 ml of a 1N aqueous sodium hydroxide was added to the reaction solution under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and brine, dried over magnesium sulfate and concentrated to dryness. A mixed solution of tert-butyl methyl ether and hexane was added to the residue, and the crystals were collected by filtration, to give 2.23 g of the title compound. 1H-NMR(DMSO-d6) delta (ppm): 2.90(3H, s), 7.21(1H, d, J=8.4 Hz), 8.11(1H, d, J=8.4 Hz), 8.39(1H, s), 10.01(1H, s), 12.71(1H, br s)

Reference： [1]Patent: WO2019/147783,2019,A1 .Location in patent: Paragraph 00170; 00171
[2]Patent: US2002/128480,2002,A1
[3]Patent: EP1258252,2002,A1
[4]Patent: US2004/18192,2004,A1

2
[ 289483-81-4 ]
[ 530-62-1 ]
[ 289483-82-5 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; hydroxylamine hydrochloride; triethylamine; In N-methyl-acetamide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; hexane; tert-butyl methyl ether;	Production Example 6 3-Cyano-4-methyl-7-nitro-1H-indole Into 100 ml of dimethylformamide was dissolved 2.21 g (10.8 mmol) of the compound of Production Example 5 followed by adding 900 mg (13.0 mmol) of hydroxylamine hydrochloride and 1.05 ml (13.0 mmol) of pyridine thereto. After heating at 60 C. under stirring for 40 minutes, 53.9 mmol of 1,1'-carbonyldiimidazole (53.9 mmol) were added to the reaction solution under ice-cooling. After heating at 60 C. for further 30 minutes under stirring, 3.0 ml (21.5 mmol) of triethylamine was added to the reaction solution followed by heating at the same temperature for further 1 hour under stirring. To the reaction mixture was added 50 ml of ice water under ice-cooling followed by extracting with ethyl acetate. The organic layer was washed with water and brine successively, dried over magnesium sulfate and concentrated to dryness. To the resulting residue was added a mixed solution of tert-butyl methyl ether and hexane, and the resulting crystals were collected by filtration to give 1.95 g of the title compound. 1H-NMR(DMSO-d6) delta (ppm); 2.78(3H,s), 7.22(1H,d,J=8.0 Hz) 8.14(1H,d,J=8.0 Hz), 8.41(1H,s), 12.76(1H,brs).
	With pyridine; hydroxylamine hydrochloride; triethylamine; In N-methyl-acetamide; ice-water; hexane; tert-butyl methyl ether;	Production Example 6 3-Cyano-4-methyl-7-nitro-1H-indole 2.21 g (10.8 mmol) of the compound of Production Example 5 was dissolved in 100 ml of dimethylformamide, followed by adding 900 mg (13.0 mmol) of hydroxylamine hydrochloride and 1.05 ml (13.0 mmol) of pyridine. After heating under stirring at 60C for 40 minutes, 1,1-carbonyldiimidazole (53.9 mmol) was added to the reaction solution under ice-cooling. After heating under stirring at 60C for further 30 minutes, 3.0 ml (21.5 mmol) of triethylamine was added to the reaction solution and the mixture was heated under stirring at the same temperature for further one hour. 50 ml of ice-water was added to the reaction mixture solution under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and brine, dried over magnesium sulfate and concentrated to dryness. A mixed solution of tert-butyl methyl ether and hexane was added to the residue and the crystals were collected by filtration, to give 1.95 g of the title compound.1H-NMR(DMSO-d6) delta (ppm): 2.78 (3H, s), 7.22 (1H, d, J=8.0Hz), 8.14 (1H, d, J=8.0Hz), 8.41 (1H, s), 12.76 (1H, br s)
	With pyridine; hydroxylamine hydrochloride; triethylamine; In N-methyl-acetamide; ice-water; hexane; tert-butyl methyl ether;	PRODUCTION EXAMPLE 6 3-Cyano-4-methyl-7-nitro-1H-indole 2.21 g (10.8 mmol) of the compound of Production Example 5 was dissolved in 100 ml of dimethylformamide, followed by adding 900 mg (13.0 mmol) of hydroxylamine hydrochloride and 1.05 ml (13.0 mmol) of pyridine. After heating under stirring at60 C. for 40 minutes, 1,1-carbonyldiimidazole (53.9 mmol) was added to the reaction solution under ice-cooling. After heating under stirring at 60 C. for further 30 minutes, 3.0 ml (21.5 mmol) of triethylamine was added to the reaction solution and the mixture was heated under stirring at the same temperature for further one hour. 50 ml of ice-water was added to the reaction mixture solution under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and brine, dried over magnesium sulfate and concentrated to dryness. A mixed solution of tert-butyl methyl ether and hexane was added to the residue and the crystals were collected by filtration, to give 1.95 g of the title compound. 1H-NMR(DMSO-d6) delta (ppm): 2.78 (3H, s), 7.22 (1H, d, J=8.0 Hz) 8.14 (1H, d, J=8.0 Hz), 8.41 (1H, s), 12.76 (1H, br s)

Reference： [1]Patent: US2002/128480,2002,A1
[2]Patent: EP1258252,2002,A1
[3]Patent: US2004/18192,2004,A1

3
[ 289483-81-4 ]
[ 289483-82-5 ]

Yield	Reaction Conditions	Operation in experiment
89.7%		Reference Example 2A Synthesis of 3-cyano-4-methyl-7-nitro-1H-indole After dissolving 2.21 g (10.8 mmol) of the 3-formyl-4-methyl-7-nitro -1H-indole obtained in Reference Example 1A in 100 mL of dimethylformamide, 900 mg (13.0 mmol) of hydroxylamine hydrochloride and 1.05 mL (13.0 mmol) of pyridine were added. The mixture was heated and stirred at 60 C. for 40 minutes, and then 1,1'-carbonyldiimidazole (53.9 mmol) was added to the reaction mixture while cooling in an ice bath. The mixture was further heated and stirred at 60 C. for 30 minutes, and then 3.0 mL (21.5 mmol) of triethylamine was added to the reaction mixture, and heating and stirring were continued at the same temperature for 1 hour. To the reaction mixture was added 50 mL of ice water while cooling in an ice bath and extraction was performed with ethyl acetate. The organic layer was washed with water and brine in that order, dried over magnesium sulfate, and concentrated to dryness. A mixture of tert-butyl methyl ether and hexane was added to the residue, and the crystals were collected by filtration to give 1.95 g of the title compound (yield: 89.7%). 1H-NMR (DMSO-d6) delta (ppm): 2.78 (3H, s), 7.22 (1H, d, J=8.0Hz), 8.14 (1H, d, J=8.0Hz), 8.41 (1H, s), 12.76 (1H, br s).
	With bismuth(lll) trifluoromethanesulfonate; acetylhydroxamic acid; In N,N-dimethyl-formamide; at 100℃; for 16h;	A solution of Sl-2 (500 mg, 2.45 mmol), /V-hydroxyacetamide (239 mg, 3.18 mmol, 1.3 equiv), Bi(OTf)3 (80 mg, 0.123 mmol, 0.05 equiv) in DMF (6 mL) was stirred at 100 C for 16 h before it was diluted with EtOAc (100 mL). The resulting mixture was washed with brine (3 x 50 mL), dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue was used in next step without any further purification.

Reference： [1]Patent: US2007/37854,2007,A1 .Location in patent: Page/Page column 5-6
[2]Patent: WO2019/147783,2019,A1 .Location in patent: Paragraph 00170; 00172

4
[ 289483-80-3 ]
[ 68-12-2 ]
[ 289483-81-4 ]

Yield	Reaction Conditions	Operation in experiment
95.8%		Reference Example 1A Synthesis of 3-formyl-<strong>[289483-80-3]4-methyl-7-nitro-1H-indole</strong> To 12 mL (154 mmol) of dimethylformamide was added 1.5 mL (16.1 mmol) of phosphorous oxychloride at 0 C., followed by stirring at the same temperature for 20.5 hour. To the reaction mixture was then added a solution of 2.0 g (11.4 mmol) of <strong>[289483-80-3]4-methyl-7-nitro-1H-indole</strong> in dimethylformamide (20 mL) at 0 C., followed by heating and stirring at 90 C. for 21 hours. To the reaction mixture was added 100 mL of 1 N aqueous solution of sodium hydroxide to the reaction mixture while cooling in an ice bath, and extraction was performed with ethyl acetate. The organic layer was washed with water and brine in that order, dried over magnesium sulfate, and concentrated to dryness. A mixture of tert-butyl methyl ether and hexane was added to the residue, and the crystals were collected by filtration to give 2.23 g of the title compound (yield: 95.8%). 1H-NMR (DMSO-d6) delta (ppm): 2.90 (3H, s), 7.21 (1H, d, J=8.4Hz), 8.11 (1H, d, J=8.4Hz), 8.39 (1H, s), 10.01 (1H, s), 12.71 (1H, br s).

Reference： [1]Patent: US2007/37854,2007,A1 .Location in patent: Page/Page column 5

5
[ 289483-81-4 ]
[ 289483-87-0 ]

Reference： [1]Patent: WO2019/147783,2019,A1

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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 289483-81-4 ] {[proInfo.proName]}

Quality Control of [ 289483-81-4 ]

Related Doc. of [ 289483-81-4 ]

Product Details of [ 289483-81-4 ]

Safety of [ 289483-81-4 ]

Application In Synthesis of [ 289483-81-4 ]

[ 289483-81-4 ] Synthesis Path-Upstream 1~4

[ 289483-81-4 ] Synthesis Path-Downstream 1~5

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry