28020-38-4|6-Methoxypyridine-2,3-diamine| Ambeed

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CAS No. :	28020-38-4
Formula :	C₆H₉N₃O
M.W :	139.16
SMILES Code :	NC1=NC(OC)=CC=C1N
MDL No. :	MFCD06658229

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H315-H319-H332-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Yield	Reaction Conditions	Operation in experiment
0.187 g		Compound 9c was obtained as described17 using 2,6-dichloropyridine as the starting material in five steps, including methoxylation, nitration, amination, reduction, and cyclization. The overall yield of this sequence was up to 45.7%. The structure of the product was identified by 1H NMR, MS, and IR. A solution of 0.5 g (3 mmol) 6-methoxy-3-nitropyridine-2-amine 100 ml CH3OH, 2 ml H2O, and 0.1 g Pd/C (10%) are allowed to shake with H2 (3 bar) in a hydrogenation apparatus until constant pressure. After filtration, the product solution is heated with 1 ml CS2 and 0.225 g KOH until reflux. When the reaction is completed (TLC control) the solvent is evaporated under reduced pressure. The resulted solid is recrystallized from ethanol. Yield: 0.187 g (1.1 mmol), 35%, mp: 223-225 C. IR: inlMMLBox (cm-1) = 3262; 3051; 1624. 1H NMR: (200 MHz, DMSO-d6) delta (ppm) = 12.99 (s, 1H, NH); 12.54 (s, 1H, NH); 7.43-7.47 (d, 1H, J = 8.5 Hz, H arom.); 6.55-6.60 (d, 1H, J = 8.5 Hz, H arom.); 3.83 (s, 3H, CH3). 13C NMR: (50 MHz, DMSO-d6) delta (ppm) = 167.60; 160.12; 143.62; 120.17; 119.65; 103.90; 53.49
16.9 g	With potassium hydroxide; In ethanol; water; for 12.0h;Reflux;	To a solution of compound 2 (20.56 g, 148 mmol) in a mixture of EtOH (200 mL) and water (40 mL) was added KOH (9.75 g, 148 mmol) and CS2 (22.5 g, 296 mmol). The reaction mixture was stirred at reflux for 12 h. The solvents were evaporated, and the residue was purified by column chromatography on silica gel with eluent (2:98 to 10:90 MeOH/CH2Cl2), affording a gray solid product 3 (16.9 g, 63%). Rf = 0.50 (1:19 MeOH/CH2Cl2), mp 246-248 C. 1H NMR (DMSO-d6): delta 3.83 (s, 3H, OCH3), 6.56 (d, J = 8.5 Hz, 1H, Ar-H), 7.44 (d, J = 8.5 Hz, 1H, Ar-H), 12.73 (s, 2H, NH). MS (ESI): 182 ([M+H]+, 100%); MS (ESI): 180 ([M-H]-, 23%).

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Code	Phrase
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P378
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P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
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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:
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
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P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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CAS No.: 28020-38-4

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CAS No.: 28020-38-4

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[ 28020-38-4 ] Synthesis Path-Downstream 1~1

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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