[ CAS No. 25369-32-8 ]

Name: 25369-32-8|7-Aminoindolin-2-one|97%
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Quality Control of [ 25369-32-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 25369-32-8 ]

CAS No. :	25369-32-8	MDL No. :	MFCD12924258
Formula :	C₈H₈N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	148.16 g/mol	Pubchem ID :	6423312
Synonyms :

Safety of [ 25369-32-8 ]

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 [ 25369-32-8 ]

Downstream synthetic route of [ 25369-32-8 ]

[ 25369-32-8 ] Synthesis Path-Downstream 1~16

2
[ 25369-31-7 ]
[ 25369-32-8 ]

Yield	Reaction Conditions	Operation in experiment
76.77%	With Pd/C (30%); hydrogen; In methanol; at 20.0℃; for 4.0h;	To a solution of <strong>[25369-31-7]7-nitroindolin-2-one</strong> in methanol (1.0 gm/60 ml), added Pd/C (300 mg, 30 wt %). H2 gas maintained with pressure using hydrogen gas balloon, solution stirred for 4 hours at RT. The catalyst was removed by filtration over celite. The filtrate was concentrated in vacuo to give crude product, which was washed with diethyl ether to afford compound 7-aminoindolin-2-one; YD: 76.77%; mp:248-251 C.; R1 0.6 (CHC13:MeOH:: 9.0:1.0). 1H NMR (DMSO-d6) 200 MHz, delta 3.382 (s, 2H), 4.794 (s, 2H), 6.453- 6.498 (m, 2H), 6.673 (t, J=8.0 Hz, 1H), 9.906 (s, 1H). MS (ESI): mlz 146.8 [M-H]-.

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 4674 - 4686
[2]European Journal of Medicinal Chemistry,2014,vol. 85,p. 268 - 288
[3]Patent: US2013/281451,2013,A1 .Location in patent: Paragraph 0157
[4]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1223 - 1226

3
[ 25369-32-8 ]
[ 98-60-2 ]
4-chloro-N-(2-oxo-2,3-dihydro-1H-indol-7-yl)-benzenesulfonamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1223 - 1226

4
[ 25369-32-8 ]
[ 98-59-9 ]
N-(1,3-Dihydro-2H-indole-2-one-7-yl)-4-methylbenzenesulfonamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1223 - 1226

5
[ 25369-32-8 ]
[ 98-68-0 ]
4-methoxy-N-(2-oxo-2,3-dihydro-1H-indol-7-yl)-benzenesulfonamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1223 - 1226

6
[ 25369-32-8 ]
[ 98-74-8 ]
[ 292635-74-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1223 - 1226

7
[ 16629-19-9 ]
[ 25369-32-8 ]
N-(2-oxo-2,3-dihydro-1H-indol-7-yl)thiophene-2-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With pyridine; at 0 - 20℃; for 2.0h;	Reference Example 9 N-(2-Oxo-2,3-dihydro-1H-indol-7-yl)thiophene-2-sulfonamide [Show Image] To a mixture of <strong>[25369-32-8]7-amino-2-oxo-2,3-dihydro-1H-indole</strong> (1.53 g) and pyridine (20 mL) was added thiophene-2-sulfonyl chloride (2.26 g) at 0C, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, 10% aqueous citric acid solution was added, and the resulting crystals were filtrated, washed with water and dried. The obtained crystals were subjected to silica gel column chromatography, and eluted with ethyl acetate. The eluate was treated with activated carbon and concentrated to give the title compound (2.93 g, yield 97%) as colorless crystals. The crystals were recrystallized from tetrahydrofuran-hexane. melting point >230C (decomposition).

Reference： [1]Patent: EP1873144,2008,A1 .Location in patent: Page/Page column 61

8
[ 607-35-2 ]
[ 25369-32-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1223 - 1226

9
[ 25369-32-8 ]
4-amino-N-(2-oxo-2,3-dihydro-1H-indol-7-yl)-benzenesulfonamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1223 - 1226

10
[ 25369-32-8 ]
[ 3932-97-6 ]
7-(4-Chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-1,3-dihydro-indol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With triethylamine;zinc(II) chloride; In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol; at 0 - 20℃;	<strong>[25369-32-8]7-amino-oxindole</strong> (910 mg, 6.1 mmol) was added portionwise to a solution of 5-trifluoromethyl-2,4-dichloropyrimidine (1.33 g, 1 eq) and ZnCl2 (6.1 mL of a 1M solution in ether) in 1:1 DCE/t-butanol (30 mL) at 0 C. After 15 minutes a solution of Et3N (0.94 mL, 1.1 eq) in 1:1 DCE/t-butanol (10 mL) was added dropwise. The reaction was allowed to warm to RT overnight. The reaction was then concentrated and the product triturated from methanol as a green solid 1.61 g (81%). 1H NMR (DMSO-d6, 400 MHz) delta 3.51 (s, 2H), 6.92 (m, 1H), 7.08 (d, J=7.5 Hz, 2H), 8.66 (s, 1H), 10.10 (s, 1H), 10.17 (s, 1H); HPLC ret. time: 5.870 min. LRMS (M+) 329.1, 331.1.

Reference： [1]Patent: US2005/256125,2005,A1 .Location in patent: Page/Page column 30

11
[ 64-18-6 ]
[ 25369-32-8 ]
[ 1168721-33-2 ]

Yield	Reaction Conditions	Operation in experiment
71%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 2.0h;	To a suspension of 7-aminooxindole (32 mg, 0.22 mmol) in CH2Cl2 (1 mL) was added EDC (83 mg, 0.43 mmol) and formic acid (12 mg, 0.26 mmol). The reaction mixture was stirred at rt for 2 h and then filtered. The filter cake was washed with diethyl ether to give the title compound as a grey solid (27 mg, 71%). 1H NMR (400MHz, CD3OD) delta 8.23 (s, IH), 7.20 (d, IH, J= 8 Hz), 7.15 (d, IH, J= 8 Hz), 7.02 (t,IH, J= 8 Hz), 3.59 (s, 2H); MS ESI [M + H]+, calcd for [C9H8N2O2 +H]+ 177.07; found m/z 177.0.

Reference： [1]Patent: WO2009/79767,2009,A1 .Location in patent: Page/Page column 126

12
[ 25369-32-8 ]
[ 1795-48-8 ]
[ 1168721-29-6 ]

Yield	Reaction Conditions	Operation in experiment
61%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃;	To a suspension of <strong>[25369-32-8]7-aminoindolin-2-one</strong> (60 mg, 0.41 mmol) in THF (3 mL) was added DIPEA (0.28 mL, 1.62 mmol), and 2-isocyanatopropane (0.05 mL, 0.49 mmol). The mixture was stirred at rt overnight then filtered. The filter cake was washed with diethyl ether to give the title compound as a pale solid (57.3 mg, 61%). 1H NMR (400 MHz, CD3OD) delta 7.09-7.04 (m, 2H), 6.99-6.95 (m, IH), 3.57 (s, 2H), 2.64 (m, IH), 1.20 (d, 6H, J = 6.4Hz). MS ESI [M + H]+, calcd for [Ci2H15N3O2 +H]+ 234.12; found m/z 234.0.

Reference： [1]Patent: WO2009/79767,2009,A1 .Location in patent: Page/Page column 125

13
[ 669050-69-5 ]
[ 25369-32-8 ]
[ 1168721-50-3 ]

Yield	Reaction Conditions	Operation in experiment
28%	With piperidine; In methanol; at 60℃; for 4h;	A 13 mg (0.0877 mmol) solution of 7-aminooxindole (T. Nakashima & I. Suzuki, Chem. Pharm. Bull. (1969) 11, 2293) and lH-indazole-6-carbaldehyde (14 mg, 0.0965 mmol) in MeOH (1.0 mL) was treated with piperidine (~1 uL, 0.00877 mmol) and the reaction was heated to 60 0C for 4 hours. The MeOH was then removed in vacuo and the residue treated with 95:5 CH2Cl2/Me0H. The resulting precipitate was filtered and washed with 95:5 CH2Cl2MeOH to obtain the title compound as a orange powder (6.7 mg, 28 %). 1H NMR (400 MHz, CD3OD) delta 8.14 (s, IH), 7.94-7.87 (m, 3H), 7.46 (d, J = 8.19 Hz, IH), 7.31 (d, J = 7.63 Hz, IH), 6.90 <n="134"/>(d, J = 7.89 Hz, IH), 6.81 (t, J = 7.79 Hz, IH); MS ESI 277.0 [M + H]+, calcd for [C16H12N4O + H]+ 277.11.

Reference： [1]Patent: WO2009/79767,2009,A1 .Location in patent: Page/Page column 132

14
[ 25369-32-8 ]
[ 5416-93-3 ]
[ 1236291-28-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 4674 - 4686

15
[ 868171-67-9 ]
[ 25369-32-8 ]
1-(4-fluorophenyl)-2-oxo-N-(2-oxoindolin-7-yl)-1,2-dihydropyridine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In N,N-dimethyl-formamide; acetonitrile; at 20℃; for 3.0h;	General procedure: Appropriate aminoindolin-2-one (1equiv) was added to a mixture of appropriate 3-amino-3-oxopropanoic acid/2-pyridone acid/4-pyridone acid (1equiv), TBTU (1.5equiv) and TEA (3equiv) in DMF/acetonitrile (1:3, 0.16M). The resulting reaction mixture was stirred at room temperature for 3h. Reaction mixture was then concentrated in vacuo. Title compound was collected as solid by filtration and dried.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 84,p. 312 - 334

16
[ 25369-32-8 ]
[ 4695-57-2 ]
[ 1621584-47-1 ]

Yield	Reaction Conditions	Operation in experiment
73%	In acetonitrile; at 70 - 80℃;	General procedure: Oxalyl chloride (6.61mmol) was added dropwise into a stirred solution of the appropriate benzamide (2.6mmol) in CH2Cl2 (10mL). The mixtures were heated at reflux for 20-22h. Then, solvents were evaporated in vacuo to give the respective crude benzoyl isocyanates 4a-k, which were used immediately in the next step without purification. Aminoindolin-2-one (2.8mmol) was added into a stirred solution of the appropriate benzoyl isocyanate (2.8mmol) in acetonitrile (10mL). After addition, each mixture was heated at 70-80C for 2-3h. The solid products were each filtered, washed with acetonitrile, and air dried.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 85,p. 268 - 288

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
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P251	Pressurized container: Do not pierce or burn, even after use.
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P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
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P270	Do not eat, drink or smoke when using this product.
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P272	Contaminated work clothing should not be allowed out of the workplace.
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P281	Use personal protective equipment as required.
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P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
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P308	IF exposed or concerned:
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P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P420	Store away from other materials.
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
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. 25369-32-8 ]

Quality Control of [ 25369-32-8 ]

Related Doc. of [ 25369-32-8 ]

Product Details of [ 25369-32-8 ]

Safety of [ 25369-32-8 ]

Application In Synthesis of [ 25369-32-8 ]

[ 25369-32-8 ] Synthesis Path-Downstream 1~16

Related Parent Nucleus of [ 25369-32-8 ]

Indolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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