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Chemical Structure| 50712-70-4 Chemical Structure| 50712-70-4

Structure of 50712-70-4

Chemical Structure| 50712-70-4

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Product Details of [ 50712-70-4 ]

CAS No. :50712-70-4
Formula : C8H6ClN
M.W : 151.59
SMILES Code : CC1=C(C=C(Cl)C=C1)C#N
MDL No. :MFCD00045599
InChI Key :HFBZPKYQUFLCEL-UHFFFAOYSA-N
Pubchem ID :142743

Safety of [ 50712-70-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H319
Precautionary Statements:P305+P351+P338

Application In Synthesis of [ 50712-70-4 ]

* 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.

  • Downstream synthetic route of [ 50712-70-4 ]

[ 50712-70-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 50712-70-4 ]
  • [ 50712-69-1 ]
YieldReaction ConditionsOperation in experiment
77.1% With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 4h;Reflux; 2-(bromomethyl)-5-chlorobenzonitrile; 5-chloro-2-methylbenzonitrile (3.02 g, 20 mmol) was dissolved in 70 mL carbon tetrachloride. NBS (N-bromosuccinimide) (3.916 g, 22 mmol) and BPO (benzoyl peroxide) (0.194 g) were added, and refluxed for 4 h. The hot solution was subjected to filtration. The filtrate was spinned to dryness, and then dissolved in 20 mL chloroform, washed with saturated sodium carbonate solution and water, dried with Na2SO4, spinned to dryness, and subjected to column chromatography eluted with petroleum ether to afford 3.532 g white solid with a yield of 77.1%.
77.1% With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 4h;Reflux; Example 10 The preparation of (R)-2-[[7-(3-aminopiperidin-1-yl)-3-methyl-2-oxo-2,3-dihydroimidazo[4,5-b]pyridin-1-yl]methyl]-5-chlorobenzonitrile (Compound 10) trifluoroacetate 5-chloro-2-methylbenzonitrile (3.02 g, 20 mmol) was dissolved in 70 mL carbon tetrachloride. NBS (N-bromosuccinimide) (3.916 g, 22 mmol) and BPO (benzoyl peroxide) (0.194 g) were added, and refluxed for 4 h. The hot solution was subjected to filtration. The filtrate was spinned to dryness, and then dissolved in 20 mL chloroform, washed with saturated sodium carbonate solution and water, dried with Na2SO4, spinned to dryness, and subjected to column chromatography eluted with petroleum ether to afford 3.532 g white solid with a yield of 77.1 %.
54% With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 4h;Reflux; 5-chloro-2-methylbenzonitrile (2.5 g, 16.5 mmol) was dissolved in carbon tetrachloride (40 mL), and N-bromosuccinimide (2.94 g, 16.5 mmol) was added, followed by benzoyl peroxide (0.107 g, 0.33 mmol). The mixture was refluxed for 4 h, and the white succinimide residue was filtered off. The solvent was evaporated under reduced pressure and the residue was chromatographed on silica gel eluting with Hexanes:EtOAc (1:0 to 9:1). One pure fraction was collected (2.05 g, 54 % yield) as a white crystalline solid. [0137] 1H NMR (400 MHz, CDCl3) delta 7.65 (1H, d), 7.57 (1H, dd), 7.50 (1H, d), 4.60 (2H, s).
54% With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 4h;Reflux; a) 2-(Bromomethyl)-5-chlorobenzonitrile5-chloro-2-methylbenzonitrile (2.5 g, 16.5 mmol) was dissolved in carbon tetrachloride (40 ml_), and N-bromosuccinimide (2.94 g, 16.5 mmol) was added, followed by benzoyl peroxide (0.107 g, 0.33 mmol). The mixture was refluxed for 4 h, and the white succinimide residue was filtered off. The solvent was evaporated under reduced pressure and the residue was chromatographed on silica gel eluting with Hexanes:EtAcO (1 :0 to 9:1 ). One pure fraction was collected (2.05 g, 54 % yield) as a white crystalline solid.1 H NMR (400 MHz, CDCI3) ? 7.65 (1 H, d), 7.57 (1 H, dd), 7.50 (1 H, d), 4.60(2H, s).
Product distribution / selectivity; Preparative Example 67. Preparation of Table 1 Compound No. 236; Bromide 88, prepared from 5-chloro-2-methylbenzonitrile (Matrix Scientific) was combined with amine salt 6 according to the method of Preparative Example 13 to give 89. Nitrile 89 (377 mg, 0.75 mmol) was then dissolved in absolute ethanol (3 ml_). Hydroxylamine hydrochloride (150 mg, 1.5 mmol) and diisopropylethylamine (261 mul_, 194 mg, 1.5 mmol) were added. The reaction mixture was stirred at reflux for 16 hours. The reaction mixture was cooled to room temperature, neutralized with saturated sodium bicarbonate solution, and extracted with ethyl acetate. The organic solution was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give 90 as a yellow solid. Purification by silica gel chromatography (8% (7 M ammonia in methanol) in dichloromethane) gave 90 (167 mg, 42% yield). MS: [M + H]+ = 536. EPO <DP n="146"/>The nitro compound 90 was converted to 91 following procedures given in Preparative Examples 5 and 19, substituting methylamine for cyclopropylamine in the final step. MS: [M + H]+ = 651.
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;Heating / reflux; Reference example 71; (1); To 5-chloro-2-methylbenzonitrile (7.8g) in carbon tetrachloride (50ml) were added N-bromosuccinimide (9.26g) and benzoylperoxide (515mg), and the mixture was stirred under reflux overnight. The reaction mixture was cooled and purified with silica gel column chromatography (hexane:ethyl acetate=30:1) to give compound (2) (8.87g) as a yellow transparent oil. 1HNMR(400MHz/CDCl3)delta(ppm):4.60(s,2H),7.50(d,1H,J=8.5Hz),7.57(dd,1H,J=2.3, 8.5Hz),7.65(d,1H,J=2.3Hz)

 

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