1309788-49-5|6,6-Dimethyl-4,5,6,7-tetrahydro-1H-indazole| Ambeed

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CAS No. :	1309788-49-5
Formula :	C₉H₁₄N₂
M.W :	150.22
SMILES Code :	CC1(C)CCC2=C(NN=C2)C1
MDL No. :	MFCD26407116

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Yield	Reaction Conditions	Operation in experiment
99%	With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 0.75h;	Step 33 -Io do -6 ,6 -dimethyl-4 ,5 ,6 ,7 -tetrahydro - 1 H-indazoleTo a solution of 6,6-dimethyl-4,5,6,7-tetrahydro-lH-indazole (0.50 g, 3.33 mmol) in DMF (8 mL) at room temperature was added powdered potassium hydroxide (560 mg, 10.0 mmol) and iodine (1.69 g, 6.66 mmol). The maroon reaction mixture was stirred at room temperature for 45 min then quenched with 10%> aqueous Na2S203, diluted with water and extracted with EtOAc (2x). The combined organics were washed with water (3x), dried over MgS04 and concentrated to afford 920 mg (99%>) of 3-iodo-6,6-dimethyl-4,5,6,7-tetrahydro-lH-indazole as a light yellow waxy solid. 1H NMR (CDC13, 300 MHz): ? (ppm) 2.44 (s, 2H), 2.35 (t, J=6.4 Hz, 2H), 1.55 (t, J=6.4 Hz, 2H), 1.01 (s, 6H).
	With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 4h;	Under a nitrogen atmosphere, to a suspension of sodium hydride (28 g, 697 mmol) in tetrahydrofuran (500 ml) was added dropwise a solution of 3,3-dimethylcyclohexanone (80 g, 634 mmol) in tetrahydrofuran (250 ml) under ice-cooling over about 1 hr, and the mixture was stirred for 1 hr. Then, a solution of ethyl formate (99 g, 1.3 mol) in tetrahydrofuran (250 ml) was added dropwise over about 1 hr, and the mixture was stirred under ice-cooling for 1 hr, and at room temperature for 1 hr. To the reaction mixture were added water and ethyl acetate, and the organic layer was separated and extracted with 2 N aqueous sodium hydroxide solution. The aqueous layer was acidified with concentrated hydrochloric acid, and extracted with ethyl acetate. Then, the organic layer was washed with saturated brine, and dried over sodium sulfate. Sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure to give 4,4-dimethyl-2-oxocyclohexanecarbaldehyde. To a solution of the obtained 4,4-dimethyl-2-oxocyclohexanecarbaldehyde in methanol (376 ml) was added dropwise a solution of hydrazine monohydrate (31 ml, 640 mmol) in methanol (31 ml) with heating under reflux over about 1 hr, and the mixture was stirred for 15 min. The reaction mixture was concentrated under reduced pressure, ethyl acetate and water were added, and the organic layer was separated. Then, the organic layer was washed with saturated brine, and dried over sodium sulfate. Sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure to give 6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazole. To a solution of the obtained 6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazole in N,N-dimethylformamide (1.4 L) were added iodine (232 g, 915 mmol) and potassium hydroxide (121 g, 1.8 mol) at room temperature, and the mixture was stirred for about 4 hr. Then, under ice-cooling, an aqueous solution (800 ml) of sodium hydrogensulfite (80 g) was added dropwise. Water (2 L) was added, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over sodium sulfate. Sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. Then, hexane (350 ml) was added to the residue, and the mixture was stirred at room temperature. The precipitated crystals were collected by filtration, washed with hexane, and dried under reduced pressure to give 3-iodo-6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazole (41 g, yield 23%).1H-NMR (400 MHz, DMSO-d6) delta: 0.94 (s, 6H), 1.47 (t, 2H, J=6.38 Hz), 2.21 (t, 2H, J=6.38 Hz), 2.33 (s, 2H), 12.69 (s, 1H).
3.95 g	With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 5h;	Step 3 : 3-Iodo-6,6-dimethyl-4,5,6,7-tetrahydro-lH-indazole: To a stirred solution of step 2 intermediate (13.3 g, 88.54 mmol) in dry N,N-dimethylformamide (177 ml), iodine (15.74 g, 61.98 mmol) was added followed by addition of potassium hydroxide (13.88 g, 247.9 mmol) at room temperature and the reaction mixture was stirred for 5 h at room temperature. The reaction mixture was cooled in ice bath, saturated solution of sodium thiosulfate (100 ml) was added and the mixture was extracted with ethyl acetate (3 x 200 ml). The combined organic layer was washed with water (200 ml), dried over sodium sulfate and filtered. The mixture was concentrated under reduced pressure and purified by column chromatography to yield 3.95 g of product as a pale yellow solid. 1H NMR (300 MHz, CDC13): delta 1.00 (s, 6H), 1.54 (t, J = 6.9 Hz, 2H), 2.34 (t, / = 6.3 Hz, 2H), 2.49 (s, 2H), 1 1.89 (s, 1H).

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CAS No.: 1309788-49-5

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CAS No.: 1309788-49-5

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[ 1309788-49-5 ] 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