Home Cart 0 Sign in  

[ CAS No. 52898-49-4 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 52898-49-4
Chemical Structure| 52898-49-4
Structure of 52898-49-4 * Storage: {[proInfo.prStorage]}

Quality Control of [ 52898-49-4 ]

Related Doc. of [ 52898-49-4 ]

SDS
Alternatived Products of [ 52898-49-4 ]
Alternatived Products of [ 52898-49-4 ]

Product Details of [ 52898-49-4 ]

CAS No. :52898-49-4 MDL No. :MFCD02684314
Formula : C10H13NO3 Boiling Point : 345.6°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :195.22 g/mol Pubchem ID :15105748
Synonyms :

Safety of [ 52898-49-4 ]

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 [ 52898-49-4 ]

  • Downstream synthetic route of [ 52898-49-4 ]

[ 52898-49-4 ] Synthesis Path-Downstream   1~17

  • 3
  • [ 52898-49-4 ]
  • [ 37610-80-3 ]
  • [ 147030-66-8 ]
  • 4
  • [ 100-09-4 ]
  • [ 1117-97-1 ]
  • [ 52898-49-4 ]
YieldReaction ConditionsOperation in experiment
98% General procedure: A solution of NHMe(OMe) (0.360 g, 6.0 mmol) and benzoic acid (0.244 g, 2.0 mmol) was stirred in dry toluene (10 mL) at 0 C for 10 min. A solution of PCl3 (0.137 g, 1.0 mmol) in dry toluene (2 mL) was then added dropwise to the mixture. The mixture was warmed to r.t. slowly and then stirred at 60 C for 0.5 h. When the reaction was complete (TLC monitoring), the mixture was cooled to r.t. The mixture was then quenched with sat. NaHCO3 soln (20 mL) and extracted with EtOAc (3 × 10 mL). The combined organic layers were dried (anhyd MgSO4). The solvent was removed in vacuo.The product was purified by column chromatography (silica gel, petroleum ether-EtOAc, 3:2) to give pure 3a as a colorless oil; yield: 320 mg (97%).
89% With Bromotrichloromethane; 4-(diphenylphosphino)-benzyltrimethylammonium bromide; triethylamine; In tetrahydrofuran; at 60℃; for 6h;Inert atmosphere; General procedure: IS-PPh3 (746 mg, 1.8 mmol) was dried by a vacuum pump for 2 h at 70 C. To a flask containing IS-PPh3 were added 4-methoxycarboxylic acid (152 mg, 1.0 mmol), BrCCl3 (357 mg, 1.8 mmol), benzylamine (129 mg, 1.2 mmol), triethylamine (0.14 mL, 1.0 mmol), and THF (4 mL). The obtained mixture was stirred for 6 h at 60 C under Ar atmosphere. After the reaction, diethyl ether (10 mL) and aq HCl (1 M, 2 mL) were added at 0 C and the obtained mixture was stirred for 15-30 min at room temperature. Then, the reaction mixture was poured into water (8 mL) and the obtained mixture was extracted with diethyl ether (10 mL×4). The combined organic layer was washed with water (10 mL) and brine (10 mL), and then dried over Na2SO4. After removal of the solvent under reduced pressure, N-benzyl-4-methoxybenzamide was obtained in 93% yield with 99% purity, as estimated by 1H NMR measurement. For cinnamic and aliphatic amides (entries 18-25 in Table 2) and indole-2-carboxamide (entry 16 in Table 2), the reaction mixture was poured into water (8 mL) and the obtained mixture was extracted with chloroform (10 mL×4). The combined organic layer was washed with water (10 mL) and brine (10 mL), and then dried over Na2SO4. After removal of the solvent under reduced pressure, N-benzylamide was obtained. or the recovery of IS-Ph3PO, NaCl (5.0 g) was added to the aqueous layer. The aqueous solution was extracted with CHCl3 (10 mL×5) and the combined organic layer was dried over NaSO4. After removal of the solvent, IS-Ph3PO containing a trace amount of IS-Ph3P was obtained in 95% yield.
  • 5
  • [ 53875-17-5 ]
  • [ 33613-52-4 ]
  • [ 100-68-5 ]
  • [ 52898-49-4 ]
  • 6
  • [ 70744-47-7 ]
  • [ 30289-28-2 ]
  • [ 52898-49-4 ]
  • 7
  • [ 52898-49-4 ]
  • [ 508191-77-3 ]
  • C16H12N2O4 [ No CAS ]
  • 8
  • [ 100-07-2 ]
  • [ 1117-97-1 ]
  • [ 52898-49-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; for 2h;Inert atmosphere; General procedure: To a stirred solution of acid (1 equiv) in CH2Cl2 (for a solution of0.1 mol L1) were added oxalyl chloride [(COCl)2; 1.25 equiv] and DMF (0.004 equiv) at room temperature. After 1.5 h, the solventand the excess oxalyl chloride were removed by evaporation under vacuum. CH2Cl2 (for a solution of 0.1 mol L1), N,O-dimethylhydroxylamine (1.4 equiv), and Et3N (3 equiv) were then successively added at room temperature. After 2 h, the reaction was quenched at room temperature with a saturated solution of NaHCO3 and the mixture extracted twice with CH2Cl2. The combined organic layers were then washed with a saturated solution of NH4Cl and brine. The organic layer was then dried with anhydrous MgSO4, filtered, and concentrated under vacuum to afford the crude Weinreb amine.To a stirred solution of diisopropylamine (DIPA; 3 equiv) in THF (for a solution of 0.1 mol L1) was added n-Butyl lithium (nBuLi,1.2 M in hexane, 3.1 equiv) at -78 C. After 30 min at 0 C, the medium was recooled to -78 C and freshly distilled tBu acetate (3 equiv) was added. After 30 min at -78 C, crude Weinreb amide (1 equiv) was added at this temperature. After 1 h, the reaction was quenched at room temperature with a saturated solution of NaHCO3 and the mixture extracted twice with EtOAc. The combined organic layers were then washed with a saturated solution of NH4Cl. The organic layer was then dried with anhydrous MgSO4, filtered, and concentrated under vacuum to afford the crude tert-butyl ester. To a stirred solution of tert-butyl ester (1 equiv) in acetone (10 equiv) were added acetic anhydride (15 equiv) and sulfuric acid (1 equiv) at 0 C. The medium was then warmed slowly to room temperature over 10 min. After 45 min, the reaction was quenched at room temperature with an aqueous solution containing sodium carbonate (30 equiv) and EtOAc (100 mL) was added.The biphasic medium was then stirred for 40 min (hydrolysis ofthe remaining acetic anhydride) and the aqueous layer was extracted twice with EtOAc. The combined organic layers were then washed with a saturated solution of NH4Cl. The organic layer was dried with anhydrous MgSO4, filtered and concentrated under vacuum. The crude residue was finally purified by flash chromatography silica gel using an appropriate gradient of a cyclohexane/EtOAc mixture as eluent to give the desired dioxinone.
  • 9
  • [ 109-72-8 ]
  • [ 52898-49-4 ]
  • [ 1671-76-7 ]
  • 10
  • [ 52898-49-4 ]
  • [ 591-51-5 ]
  • [ 4160-63-8 ]
  • 11
  • [ 13139-86-1 ]
  • [ 223570-55-6 ]
  • [ 52898-49-4 ]
  • 12
  • [ 52898-49-4 ]
  • [ 117423-41-3 ]
  • 2-(<i>tert</i>-butyl-dimethyl-silanyloxy)-1-(4-methoxy-phenyl)-2-pyridin-4-yl-ethanone [ No CAS ]
  • 14
  • [ 52898-49-4 ]
  • [ 250279-14-2 ]
  • [3-(4'-hydroxy-biphenyl-4-yl)-benzo[<i>b</i>]thiophen-2-yl]-(4-methoxy-phenyl)-methanone [ No CAS ]
  • 15
  • [ 29829-22-9 ]
  • OC6H5CO2NCH2CH3(1-)*Na(1+) [ No CAS ]
  • [ 52898-49-4 ]
  • 16
  • [ 93-04-9 ]
  • [ 52898-49-4 ]
  • (3-methoxynaphthalen-2-yl)(4-methoxyphenyl)methanone [ No CAS ]
  • 17
  • [ 6638-79-5 ]
  • [ 100-07-2 ]
  • [ 52898-49-4 ]
YieldReaction ConditionsOperation in experiment
89% With triethylamine; In dichloromethane; at 0 - 20℃; for 3h; EXAMPLE 3 Compound 7) N-(1-benzylpiperidin-4-yl)-7-methoxy-4-(4-methoxyphenyl)phthalazin-1-amine 3.1. N,4-dimethoxy-N-methylbenzamide; 14.7 g (151 mmol) of N,O-dimethylhydroxylamine hydrochloride are added portionwise to a solution of 25 g (147 mmol) of 4-methoxybenzoyl chloride in 450 mL of dichloromethane, stirred at 0-5 C. under nitrogen. 51 mL (370 mmol) of triethylamine are then added slowly to the mixture stirred at 0-5 C. The orange-coloured reaction medium is stirred at room temperature for 3 hours. The mixture is hydrolysed with 250 mL of water and then extracted with dichloromethane. The organic phase is washed with 100 mL of 1N HCl, 150 mL of 1N NaOH and then with water and brine. It is dried over anhydrous sodium sulfate, filtered and evaporated to dryness. 26.9 g of an orange-coloured oil are obtained, and are purified on a column of silica, eluting with dichloromethane and then with a 95/5 dichloromethane/methanol mixture. 25.4 g of a yellow oil are obtained (89% yield). LC/MS: MH+=196 (Rt=5.21 minutes) 1H NMR delta in ppm (DMSO d 6): 3.26 (s, 3H); 3.56 (s, 3H); 3.82 (s, 3H); 7.00 (d, J=8.5 Hz, 2H); 7.63 (d, J=8.5 Hz, 2H).
With triethylamine; In dichloromethane; at 0 - 20℃; for 3h; 2.3. N-4-Dimethoxy-N-methylbenzamide To a solution of 25 g (147 mmol) of 4-methoxybenzoyl chloride in 450 mL of dichloromethane, stirred at 0-5 C. under nitrogen, are added portionwise 14.7 g (151 mmol) of N7O-dimethylhydroxylamine hydrochloride. 51 mL (370 mmol) of triethylamine are then added slowly to the mixture stirred at 0-5 C. The reaction medium is stirred at room temperature for 3 hours. The mixture is hydrolyzed with 250 mL of water and is then extracted with dichloromethane. The organic phase is washed with 100 mL of 1 N HCl, 150 mL of 1 N NaOH and then with water and with brine. It is dried over anhydrous sodium sulfate, filtered and evaporated to dryness. 26.9 g of an orange oil are obtained, which are purified on a column of silica (eluent: dichloromethane/meth-anol from 100/0 to 95/5 (v/v)). 25.4 g of a yellow oil are obtained.LC/MS: MH+=196 (Rt=5.21 minutes, pH 3.1)1H NMR (DMSO-d6, 250 MHz) delta ppm: 3.26 (s, 3H); 3.56 (s, 3H); 3.82 (s, 3H); 7.00 (d, J=8.5 Hz, 2H); 7.63 (d, J=8.5 Hz, 2H).
With pyridine; In dichloromethane; at 0 - 20℃; 4-Methoxybenzoyl chloride ( 1.00 g, 5.86 mmol) was dissolved in DCM ( 15 mL) and cooled to 0C. N,0-dimethylhydroxlamine hydrochloride (686 mg, 7.03 mmol) and pyridine (0.57 mL, 7.03 mmol) were added, the mixture was warmed to room temperature and stirred over night.1 M hydrochloric acid and DCM were added and the phases were separated. After flash chromatographic separation N,4- dimethoxy-N-methylbenzamide (724 mg, 3.80 mmol) was obtained.
With pyridine; In dichloromethane; at 20℃; for 1h;Inert atmosphere; General procedure: In a 50 mL round bottom flask, equipped witha magnetic stir bar and a septum, air was displaced with a continuous nitrogenflow. Then, in approximately 10 mL of dichloromethane, 1 mmol of the appropriateacylchloride and 1.1 mmol of N,O-dimethylhydroxylamine hydrochloride weredissolved and injected into the flask using a syringe . The reaction mixturewas cooled to 0C, followed by the addition of 2.2 mmol of pyridine. The resultingmixture was stirred at ambient temperature for an hour. This mixture was then partitionedbetween brine and a 1:1 mixture of ether and dichloromethane to separate theorganic layer from the aqueous layer via separation funnel. The organic layerwas dried with sodium sulfate, and filtered into an oven dried round bottomflask, using a Buchner funnel under vacuum. The solvent of the organic layerwas then removed, using a rotary evaporator, to isolate the amide product.Structure and purity were characterized by 1H NMR.

Historical Records

Related Functional Groups of
[ 52898-49-4 ]

Amines

Chemical Structure| 152121-82-9

[ 152121-82-9 ]

N,3-Dimethoxy-N-methylbenzamide

Similarity: 0.98

Chemical Structure| 155586-39-3

[ 155586-39-3 ]

N,3,5-Trimethoxy-N-methylbenzamide

Similarity: 0.96

Chemical Structure| 155586-38-2

[ 155586-38-2 ]

N,3,4-Trimethoxy-N-methylbenzamide

Similarity: 0.93

Chemical Structure| 460747-44-8

[ 460747-44-8 ]

4-Hydroxy-N-methoxy-N-methylbenzamide

Similarity: 0.93

Chemical Structure| 130250-62-3

[ 130250-62-3 ]

N,2-Dimethoxy-N-methylbenzamide

Similarity: 0.92

Aryls

Chemical Structure| 152121-82-9

[ 152121-82-9 ]

N,3-Dimethoxy-N-methylbenzamide

Similarity: 0.98

Chemical Structure| 155586-39-3

[ 155586-39-3 ]

N,3,5-Trimethoxy-N-methylbenzamide

Similarity: 0.96

Chemical Structure| 155586-38-2

[ 155586-38-2 ]

N,3,4-Trimethoxy-N-methylbenzamide

Similarity: 0.93

Chemical Structure| 460747-44-8

[ 460747-44-8 ]

4-Hydroxy-N-methoxy-N-methylbenzamide

Similarity: 0.93

Chemical Structure| 130250-62-3

[ 130250-62-3 ]

N,2-Dimethoxy-N-methylbenzamide

Similarity: 0.92

Amides

Chemical Structure| 152121-82-9

[ 152121-82-9 ]

N,3-Dimethoxy-N-methylbenzamide

Similarity: 0.98

Chemical Structure| 155586-39-3

[ 155586-39-3 ]

N,3,5-Trimethoxy-N-methylbenzamide

Similarity: 0.96

Chemical Structure| 155586-38-2

[ 155586-38-2 ]

N,3,4-Trimethoxy-N-methylbenzamide

Similarity: 0.93

Chemical Structure| 460747-44-8

[ 460747-44-8 ]

4-Hydroxy-N-methoxy-N-methylbenzamide

Similarity: 0.93

Chemical Structure| 130250-62-3

[ 130250-62-3 ]

N,2-Dimethoxy-N-methylbenzamide

Similarity: 0.92

Ethers

Chemical Structure| 152121-82-9

[ 152121-82-9 ]

N,3-Dimethoxy-N-methylbenzamide

Similarity: 0.98

Chemical Structure| 155586-39-3

[ 155586-39-3 ]

N,3,5-Trimethoxy-N-methylbenzamide

Similarity: 0.96

Chemical Structure| 155586-38-2

[ 155586-38-2 ]

N,3,4-Trimethoxy-N-methylbenzamide

Similarity: 0.93

Chemical Structure| 118779-14-9

[ 118779-14-9 ]

N,3,4,5-Tetramethoxy-N-methylbenzamide

Similarity: 0.92

Chemical Structure| 130250-62-3

[ 130250-62-3 ]

N,2-Dimethoxy-N-methylbenzamide

Similarity: 0.92