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Structure of 54367-67-8

Chemical Structure| 54367-67-8

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Product Details of [ 54367-67-8 ]

CAS No. :54367-67-8
Formula : C5H5BrN2O2
M.W : 205.01
SMILES Code : O=C(C1=C(Br)N(C)N=C1)O
MDL No. :MFCD22052492
InChI Key :NEWNBNRLTJOGAQ-UHFFFAOYSA-N
Pubchem ID :59679572

Safety of [ 54367-67-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 54367-67-8 ]

* 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 [ 54367-67-8 ]

[ 54367-67-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 105486-72-4 ]
  • [ 54367-67-8 ]
YieldReaction ConditionsOperation in experiment
92% Step 2. Synthesis of 5-bromo-1-methyl-1H-pyrazole-4-carboxylic acid A suspension of <strong>[105486-72-4]ethyl 5-bromo-1-methyl-1H-pyrazole-4-carboxylate</strong> (8.00 g, 34.3 mmol) in tetrahydrofuran (60 mL), water (20 mL) and ethanol (20 mL) was treated with lithium hydroxide monohydrate (3.17 g, 75.5 mmol) and stirred for 4 hours at room temperature. Removal of solvents under reduced pressure provided a white solid residue, which was diluted with water (50 mL), washed with diethyl ether (50 mL) and adjusted to pH 2.5 with aqueous 6 N hydrochloric acid. The thick suspension was extracted with 2-methyltetrahydrofuran (2*125 mL), and the combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to provide the product as an off-white solid. Yield: 6.49 g, 31.7 mmol, 92%. LCMS m/z 205.2 (M+1). 1H NMR (500 MHz, DMSO-d6) delta 3.86 (s, 3H), 7.91 (s, 1H), 12.64 (br s, 1H).
91.05% With water; sodium hydroxide; In methanol; at 25℃; for 3h; [0939] to a solution of compound 163b (600 mg, 2.57 mmol) in MeOH (10 ml) and H2O (10 ml) was added NaOH (514 mg, 12.85 mmol). The mixture was stirred at 25 C for 3h. The reaction mixture was concentrated and added 20 ml of water, the mixture was extracted with mtbe (10 ml x 2), the aqueous layer was acidified by in HCl to ph ~ 2-3 at 0 C, and extracted with EtOAc (20 ml x 2), the organic phase was dried over Na2SO4, concentrated to give a residue. Compound 163d (480 mg, yield: 91.05%) was obtained as a white solid. 1H NMR (400mhz, DMSO-d6) delta 12.65 (s, 1h), 8.13 (s, 1h), 3.82 (s, 3h).
Step 2. (5-Bromo-1-methyl-1H-pyrazol-4-yl)-(octahydro-quinolin-1-yl)-methanone; To a solution of <strong>[105486-72-4]5-bromo-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester</strong> (6.9 g, 29.6 mmol) in CH3OH (25 mL) and water (25 mL) was added LiOH (0.78 g, 32.6 mmol). The reaction mixture was stirred at reflux for 4 h, and then the solution was concentrated under reduced pressure to remove the methanol. The residue was diluted with water and the solution was acidified to pH 2 with concentrated HCl (3 mL). The resulting mixture was then extracted with ethyl acetate. The combined organic extracts were concentrated in vacuo to give 5-bromo-1-methyl-1H-pyrazole-4-carboxylic acid, which was used without further purification.
 

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