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[ CAS No. 54903-16-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 54903-16-1
Chemical Structure| 54903-16-1
Chemical Structure| 54903-16-1
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Product Details of [ 54903-16-1 ]

CAS No. :54903-16-1 MDL No. :MFCD11179328
Formula : C8H5NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :BZRKWTCIDCRBMY-UHFFFAOYSA-N
M.W : 179.13 Pubchem ID :391472
Synonyms :

Calculated chemistry of [ 54903-16-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 43.79
TPSA : 83.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.85
Log Po/w (XLOGP3) : 0.69
Log Po/w (WLOGP) : 0.82
Log Po/w (MLOGP) : 0.49
Log Po/w (SILICOS-IT) : 1.38
Consensus Log Po/w : 0.85

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.83
Solubility : 2.64 mg/ml ; 0.0147 mol/l
Class : Very soluble
Log S (Ali) : -2.02
Solubility : 1.72 mg/ml ; 0.00963 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.19
Solubility : 1.15 mg/ml ; 0.0064 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.24

Safety of [ 54903-16-1 ]

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 [ 54903-16-1 ]

* 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 [ 54903-16-1 ]

[ 54903-16-1 ] Synthesis Path-Downstream   1~37

YieldReaction ConditionsOperation in experiment
84.6% With sodium carbonate; In water; at 45 - 80℃; General procedure: Weigh 7.8 g (0.05 mol) of 3-amino-4-hydroxybenzoic acid,Add to a solution of 8.5 g (0.08 mol) of anhydrous sodium carbonate in 45 mL of water with stirring.Heating in a 45 C oil bath, adding 7.1 g of methyl chloroformate dropwise, plus,Stirring was continued for half an hour and then allowed to warm to 80 C overnight. The next day,Acidified to pH 2~3 under ice water cooling, filtered solids, washed with a small amount of cold water.Drying a light brown powdery solid 7.5 g (83.3%),
Also, the invention provides a compound selected from the group consisting of: ... {2-(tert-Butyldimethylsilanyloxy)-3-[4-(4-fluorobenzyl)piperidin-1-yl]propylamine; Methyl 2-oxo-2,3-dihydrobenzoxazole-6-carboxylate; 2-Oxo-2,3-dihydrobenzoxazole-6-carboxylic acid; 2-Oxo-2,3-dihydrobenzoxazole-6-carboxylic acid [3-(4-benzylpiperidin-1-yl)-2-(tert-butyldimethylsilanyloxy)propyl]amide; 2-Oxo-2,3-dihydrobenzoxazole-6-carboxylic acid [3-(4-(4-fluorobenzyl)piperidin-1-yl)-2-(tert-butylimethylsilanyloxy)propyl]amide; 2-Oxo-2,3-dihydrobenzoxazole-6-carbothioic acid [3-(4-benzylpiperidin-1-yl)-2-(tert-butyldimethylsilanyloxy)propyl]amide; 2-Oxo-2,3-dihydrobenzooxazole-6-carbothioic acid [3-(4-benzylpiperidin-1-yl)-2-hydroxypropyl]amide; 6-(2-Azido-1-hydroxyethyl)-3H-benzoxazol-2-one; ...
  • 3
  • [ 54903-16-1 ]
  • 2-amino-1-(3,4,5-trimethoxyphenyl)ethanol acetic acid salt [ No CAS ]
  • 2-oxo-2,3-dihydro-benzooxazole-6-carboxylic acid [2-hydroxy-2-(3,4,5-trimethoxy-phenyl)-ethyl]-amide [ No CAS ]
  • 4
  • [ 2374-03-0 ]
  • [ 54903-16-1 ]
  • 5
  • [ 54903-16-1 ]
  • 2-oxo-2,3-dihydro-benzooxazole-6-carboxylic acid amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
35.3% Example 7; 4-Benzyl-piperidine-l-carboxylicacid(2-oxo-2,3-dihydro-benzooxazoIe-6-carbonyl)-amide; 7a) 2-Oxo-2,3-dihydro-benzooxazole-6-carboxylic acid amide; To a stirred solution of 0.37 g (2.06 mmol) of 2-oxo-2,3-dihydro-benzooxazole-6-carboxylic acid [EurJ.Med.Chem.Chim. Ther., 9, 491-492. (1974)], 13 ml of 1,4-dioxane and 0.1 ml of dimethylformamide 1.35 ml (18 mmol) of thionyl chloride is added droep wise below 10 C, and the reaction mixture is stirred at room temperature for 24 h. Then 10 ml of 25 % ammonium hydroxide solution is added drop wise to the mixture. The reaction mixture is concentrated and the residue is purified by column chromatography using Kieselgel 60 aes adsorbent (Merck) and Chloroform : methanol = 3:1 aes eluent to yield 0.13 g (35.3 %) of the title compound. Mp.: 296 C (2-propanol).
  • 6
  • [ 54903-16-1 ]
  • [ 118-93-4 ]
  • [ 924300-28-7 ]
YieldReaction ConditionsOperation in experiment
11% With pyridine; trichlorophosphate; at 0 - 20℃; The product from step 2 (0.108 g, 0.6 mmol) and 2- hydroxyacetophenone (0.09 g, 0.66 mmol) were added to a round bottomed flask under nitrogen. Anhydrous pyridine (5 mL was added to it with stirring. The reaction mixture was cooled down using an ice bath. Phosphorus oxychloride (0.15 g, 0.99 mmol) was added and the reaction mixture was stirred at room temperature overnight. Pyridine was removed under vacuum and the residue was acidified with 1 N HCI (pH 4~5) and extracted with ethyl acetate. The solvent was EPO <DP n="91"/>evaporated in vacuo to leave a residue which was purified by silica gel column chromatography (15 g). The eluent was a mixture of ethyl acetate and hexane in 1 :1. Fraction 1 was evaporated affording pure compound (0.0192 g, 11%).
  • 7
  • [ 72752-80-8 ]
  • [ 54903-16-1 ]
YieldReaction ConditionsOperation in experiment
94% The product (1.64 g, 8.47 mmol) from step 1 was dissolved in a mixture of methanol (5 mL) and tetrahydrofuran 5 mL. Potassium hydroxide (1.25 g, 22.28 mmol) in water (6 mL) was added. The reaction mixture was refluxed at 7O0C for 3 days and 800C for 2 days. The solvent was evaporated in vacuo. Water was added and the reaction mixture was acidified with 1N HCI (pH 4~5) and extracted with ethyl acetate. The solvent was evaporated in vacuo to leave 1.43 g (94%) of pure compound. The compound was used for the following reaction without further purification.
  • 8
  • [ 207552-92-9 ]
  • [ 54903-16-1 ]
YieldReaction ConditionsOperation in experiment
80% 2-Oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylic acid. To ethyl 2-oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylate in THF (20 mL) was added LiOH (2 g in 10 mL water). The mixture was stirred at room temperature for 20 hours. The solvent was evaporated. The residue was taken up in water and acidified with 5 N HCl to pH = 5. The solid was recovered by filtration, washing with water, to provide the pure product as a tan solid (1.44 g, 80 %). LCMS (API-ES) m/z: 180 (M+H*).
  • 9
  • [ 54903-16-1 ]
  • C12H18ClN3*3ClH [ No CAS ]
  • [ 1121767-06-3 ]
YieldReaction ConditionsOperation in experiment
89% With 4-methyl-morpholine; dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 3h; c) Synthesis of compound (I-66) [Show Image] A compound 19 trihydrochloride (0.49 g, 1.40 mmol), and the known (J. Chem. Soc., 1921, viol.119, pp.1425-1432) compound 20 (0.25 g, 1.40 mmol) were dissolved in DMF (10 ml), HOBt monohydrate (0.21 g, 1.50 mmol), DMAP (17 mg, 0.14 mmol), N-methylmorpholine (0.69 ml, 6.30 mmol), and EDC (0.30 g, 1.50 mmol) were added, and the mixture was stirred at room temperature for 3 hours. Water (50 ml) was added, and the precipitated crystal was filtered, washed with water, and then dried. The resulting solid was recrystallized from ethyl acetate-methanol-diethyl ether to obtain a compound (I-66) (0.50 g, yield 89%). mp 156-158C 1H-NMR (DMSO-d6 / TMS) deltappm: 2.48-2.64 (m, 6H), 3.10-3.20 (m, 4H), 3.42 (q, J = 6.3Hz, 2H), 6.94 (d, J = 9.1Hz, 2H), 7.15 (d, J = 8.1Hz, 1H), 7.22 (d, J = 9.1Hz, 2H), 7.69-7.75 (m, 2H), 8.04 (t, J = 6.3Hz, 1H).
  • 10
  • [ 54903-16-1 ]
  • C19H26F3N3O*2ClH [ No CAS ]
  • [ 1248727-79-8 ]
YieldReaction ConditionsOperation in experiment
44% With benzotriazol-1-ol; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 15h; i. 2-oxo-2,3-dihydro-benzooxazole-6-carbonic-acid 13 (38.6 mg, 0.22 mmol), intermediate 12 (95.5 mg, 0.22 mmol) and 4-methylmorpholine (0.72 mL, 0.66 mmol) were given to DMF (3 mL). N-(3-dimethylaminopropyl)-N'- ethylcarbodiimide hydrochloride (41.4 mg, 0.22 mmol) and 1- hydroxybenzotriazolehydrate (29,2 mg, 0.2 mmol) were added at RT. It was stirred for 15 h at RT. The reaction mixture was poured onto water and extracted twice with ethyl acetate. The pooled organic phases were dried over sodium sulphate, filtrated and concentrated in vacuo until dryness. The oily residue was comminuted with diethyl ether, and the emerging solid was filtered off. A colourless solid (14, 50.4 mg, 0.09 mmol, 44%) in high purity was yielded.
  • 11
  • [ 54903-09-2 ]
  • [ 54903-16-1 ]
  • 12
  • [ 54903-16-1 ]
  • [ 873803-27-1 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; In chloroform; at 0℃;Reflux; General procedure: Method E: A solution of the appropriate acid 3a (0.91 g, 5.1 mmol) inchloroform (20 mL) was cooled to 0 C with stirring. Thionyl chloride(1.75 mL, 24 mmol) was added dropwise, and the reaction mixture was heated at reflux for 5 h. After evaporation, the resulting crude acid chloride was dissolved in dichloromethane (50 mL),to 4 C, and added dropwise to a cooled mixture of 2-amino-4,6-dimethylpyridine(0.51 g, 4.8 mmol) and triethylamine (0.95 mL, 6.8 mmol) in dichloromethane (50 mL). The reaction mixture was then stirred at room temperature for 18 h. After evaporation of dichloromethane under vacuum, the residue was treated with water and the resulting precipitate filtered, washed with water, dried and recrystallised from 95% ethanol. Compound (4b) was synthesised in an identical fashion to (4a).
  • 13
  • [ 54903-16-1 ]
  • [ 1639239-54-5 ]
  • 14
  • [ 59-49-4 ]
  • [ 54903-16-1 ]
  • 15
  • [ 54903-16-1 ]
  • tert-butyl ((2S)-1-(4-(1-aminoethyl)piperidin-1-yl)-1-oxopropan-2-yl)carbamate [ No CAS ]
  • tert-butyl ((2S)-1-oxo-1-(4-(1-(2-oxo-2,3-dihydrobenzo[d]oxazol-6-carboxamido)ethyl)piperidin-1-yl)propan-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% To a stirred solution of <strong>[54903-16-1]2-oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylic acid</strong> (0.2 g, 0.66 mmol) in DMF (1.5 mL) was added EDCI.HCl (0.191 g, 1.00 mmol), HOBt (0.091 g, 0.66 mmol) and diispropylethylamine (0.34 mL, 2.00 mmol). The solution was stirred for 10 min at 0oC. After that, tert-butyl ((2S)-1-(4-(1-aminoethyl)piperidin-1-yl)- 1-oxopropan-2-yl)carbamate (0.142 g, 0.80 mmol) was added and the reaction stirred at rt for 12 h. The progress of the reaction was monitored by TLC. After complete consumption of starting material, the reaction was quenched with water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over anhydrous Na2SO4and concentrated under reduced pressure to obtain a crude residue which was purified by column chromatography to afford tert-butyl ((2S)-1-oxo-1-(4-(1- (2-oxo-2,3-dihydrobenzo[d]oxazole-6-carboxamido)ethyl)piperidin-1-yl)propan-2- yl)carbamate (0.104 g, 33%)
  • 16
  • [ 54903-16-1 ]
  • benzyl 4-(((1R,3r,5S)-3-amino-8-aza-bicyclo[3.2.1]octan-8-yl-sulfonyl)methyl)piperidine-1-carboxylate [ No CAS ]
  • 2-oxo-N-((1R,3r,5S)-8-(piperidin-4-ylmethylsulfonyl)-8-aza-bicyclo[3.2.1]octan-3-yl)-2,3-dihydrobenzo[d]oxazole-6-carboxamide hydrochloride [ No CAS ]
  • 17
  • [ 54903-16-1 ]
  • benzyl 4-(((1R,3r,5S)-3-amino-8-aza-bicyclo[3.2.1]octan-8-yl-sulfonyl)methyl)piperidine-1-carboxylate [ No CAS ]
  • benzyl 4-(((1R,3r,5S)-3-(2-oxo-2,3-dihydrobenzo[d]oxazole-6-carboxamido)-8-aza-bicyclo[3.2.1]octan-8-ylsulfonyl)methyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 1h; Into a 25-mL round-bottom flask was placed 2-oxo-2,3-dihydro-1,3-benzoxazole- 6-carboxylic acid (100 mg, 0.56 mmol, 2.35 equiv), N,N-dimethylformamide (10 mL), HOBT (135 mg, 2.00 equiv) and EDCI (191 mg, 2.00 equiv). Then benzyl 4- [[(1R,3r,5S)-3-amino-8-azabicyclo[3.2.1]octane-8-sulfonyl]methyl]piperidine-1- carboxylate (100 mg, 0.24 mmol, 1.00 equiv) was added in several portions. After complete adddition, TEA (250 mg, 5.00 equiv) was added dropwise. The resulting solution was stirred for 1 h at room temperature. The mixture was concentrated under vacuumand the residue diluted with 10 mL of H2O. This mixture was extracted with 3x10 mL of ethyl acetate and the organic layers combined. The combined extracts were washed with 2x30 mL of brine, dried, and concentrated. The residue was chromatographed on a silica gel column with dichloromethane/methanol (10/1). This resulted in 100 mg (72%) of benzyl 4-[[(1R,3r,5S)-3-(2-oxo-2,3-dihydro-1,3- benzoxazole-6-amido)-8-azabicyclo[3.2.1]octane-8-sulfonyl]methyl]piperidine-1- carboxylate as yellow oil
  • 18
  • [ 54903-16-1 ]
  • N-[(1R,5S,6R)-3-azabicyclo[3.1.0]hexan-6-yl]methyl}-2-oxo-2,3-dihydro-1,3-benzoxazole-6-carboxamide [ No CAS ]
  • 19
  • [ 54903-16-1 ]
  • (3,5-dichlorophenyl)methyl (1R,5S,6R)-6-[(2-oxo-2,3-dihydro-1,3-benzoxazol-6-yl)formamido]methyl}-3-azabicyclo[3.1.0]hexane-3-carboxylate [ No CAS ]
  • 20
  • [ 54903-16-1 ]
  • N-[(1R,5S,6R)-3-[(2E)-3-(3,5-dichlorophenyl)prop-2-enoyl]-3-azabicyclo[3.1.0]hexan-6-yl]methyl}-2-oxo-2,3-dihydro-1,3-benzoxazole-6-carboxamide [ No CAS ]
  • 21
  • [ 54903-16-1 ]
  • N-[(1R,5S,6R)-3-[3-(3,5-dichlorophenyl)propanoyl]-3-azabicyclo[3.1.0]hexan-6-yl]methyl}-2-oxo-2,3-dihydro-1,3-benzoxazole-6-carboxamide [ No CAS ]
  • 22
  • [ 54903-16-1 ]
  • N-[(1R,5S,6R)-3-[2-(3,5-dichlorophenyl)cyclopropanecarbonyl]-3-azabicyclo[3.1.0]hexan-6-yl]methyl}-2-oxo-2,3-dihydro-1,3-benzoxazole-6-carboxamide [ No CAS ]
  • 23
  • [ 54903-16-1 ]
  • N-[(1R,5S,6R)-3-[(3,5-dichlorophenyl)methyl]carbamoyl}-3-azabicyclo[3.1.0]hexan-6-yl]methyl}-2-oxo-2,3-dihydro-1,3-benzoxazole-6-carboxamide [ No CAS ]
  • 24
  • [ 54903-16-1 ]
  • 1-(3,5-dichlorophenyl)ethyl (1R,5S,6R)-6-[(2-oxo-2,3-dihydro-1,3-benzoxazol-6-yl)formamido]methyl}-3-azabicyclo[3.1.0]hexane-3-carboxylate [ No CAS ]
  • 25
  • [ 54903-16-1 ]
  • N-[(1R,5S,6R)-3-(5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl}-2-oxo-2,3-dihydro-1,3-benzoxazole-6-carboxamide [ No CAS ]
  • 26
  • [ 54903-16-1 ]
  • [3,5-bis(trifluoromethyl)phenyl]methyl (1R,5S,6R)-6-[(2-oxo-2,3-dihydro-1,3-benzoxazol-6-yl)formamido]methyl}-3-azabicyclo[3.1.0]hexane-3-carboxylate [ No CAS ]
  • 27
  • [ 54903-16-1 ]
  • [3-cyano-5-(trifluoromethoxy)phenyl]methyl (1R,5S,6R)-6-[(2-oxo-2,3-dihydro-1,3-benzoxazol-6-yl)formamido]methyl}-3-azabicyclo[3.1.0]hexane-3-carboxylate [ No CAS ]
  • 28
  • [ 54903-16-1 ]
  • (1R,5S,6R)-6-[(2-oxo-2,3-dihydrobenzooxazole-6-carbonyl)amino]methyl}-3-azabicyclo[3.1.0]hexane-3-carboxylic acid 1-tert-butoxycarbonylpiperidin-3-ylmethyl ester [ No CAS ]
  • 29
  • [ 54903-16-1 ]
  • C22H22N4O5 [ No CAS ]
  • 30
  • [ 54903-16-1 ]
  • (1R,5S,6R)-6-[(2-oxo-2,3-dihydrobenzooxazole-6-carbonyl)amino]methyl}-3-azabicyclo[3.1.0]hexane-3-carboxylic acid 5-methylisoxazol-3-ylmethyl ester [ No CAS ]
  • 31
  • [ 54903-16-1 ]
  • tert-butyl (1R,5S,6S)-6-(aminomethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate [ No CAS ]
  • tert-butyl (1R,5S,6R)-6-[(2-oxo-3H-1,3-benzoxazol-6-yl)formamido]methyl}-3-azabicyclo[3.1.0]hexane-3-carboxylate [ No CAS ]
  • 32
  • [ 2374-03-0 ]
  • [ 79-22-1 ]
  • [ 54903-16-1 ]
YieldReaction ConditionsOperation in experiment
57% 4-amino-3-hydroxybenzoic acid (1 g, 6.5 mmol) and potassium carbonate (1.4 g, 10.5 mmol) were dissolved in distilled water (8 mL) After dissolving and stirring at 40 C, Methyl chloroformate (0.8 mL, 9.8 mmol) was slowly added dropwise, and then the temperature was raised to 80 C and stirred for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and a 2N hydrogen chloride aqueous solution was added thereto so that the pH was 2 or less. The resulting solid was filtered, washed with cold water and dried to give the title compound 32-a (0.66 mg, 57% ).
  • 33
  • [ 54903-16-1 ]
  • C15H21ClN2O3 [ No CAS ]
  • C23H24ClN3O6 [ No CAS ]
  • 34
  • [ 54903-16-1 ]
  • C16H22ClN3O2 [ No CAS ]
  • C24H25ClN4O5 [ No CAS ]
  • 35
  • [ 54903-16-1 ]
  • C15H21ClN2O3 [ No CAS ]
  • C23H24ClN3O6 [ No CAS ]
  • 36
  • [ 54903-16-1 ]
  • C17H24ClN3O2 [ No CAS ]
  • C25H27ClN4O5 [ No CAS ]
  • 37
  • [ 29684-56-8 ]
  • [ 54903-16-1 ]
  • [ 7466-54-8 ]
  • methyl N-({6-[5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl]-2-oxo-2,3-dihydro-1,3-benzoxazol-3-yl}sulfonyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% To a dry mixture of 27-1 (2-methoxyphenylhydrazide, 139 mg, 0.837 mmol), 27-2 (benzoxazol-2- one-6-carboxylic acid, 150 mg, 0.837 mmol), and HATU (318 mg, 0.837 mmol) was added THF (10 mL) to yield a hazy reddish solution. DIPEA (0.29 mL, 1.67 mmol) was added and the reaction was stirred at rt for 2 hr. Burgess reagent (499 mg, 2.09 mmol) was added one portion, and the reaction was heated to 60C overnight. An additional 499 mg Burgess reagent was added. and continued heating. After 4 hr, 2N KHSO4 (10 mL) was added and the resulting oily mixture was extracted 3X EtOAc. The combined organics were washed once with water, once with brine, filtered through cotton and concentrated to an orange solid which was purified by reverse phase chromatography, 20% - 60% MeCN/water/0.1% TFA to yield 67 mg 27-3(18%) MJ-T+ = 447.0. ?H NMR (400 MHz, DMSO) 8.02 - 7.97 (3H, m), 7.74 (1H, d, J=8.4 Hz), 7.64 (1H, t, J=8.2 Hz), 7.30 (1H, d, J=8.4 Hz), 7.18 (1H, t, J=7.4 Hz), 3.95 (3H, s), 3.39 (3H, s).
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Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Additions of Organometallic Reagents • Acetal Formation • Acid-Catalyzed α -Halogenation of Ketones • Acids Combine with Acyl Halides to Produce Anhydrides • Acyl Chloride Hydrolysis • Acyl Group Substitution • Add Hydrogen Cyanide to Aldehydes and Ketones to Produce Alcohols • Alcohol Syntheses from Aldehydes, Ketones and Organometallics • Aldehydes and Ketones Form Hemiacetals Reversibly • Aldehydes May Made by Terminal Alkynes Though Hydroboration-oxidation • Aldol Addition • Aldol Condensation • Alkenes React with Ozone to Produce Carbonyl Compounds • Alkylation of Aldehydes or Ketones • Alkylation of Enolate Ions • Amide Hydrolysis • Amide Hydrolysis • Amides Can Be Converted into Aldehydes • Amines Convert Acyl Chlorides into Amides • Anhydride Hydrolysis • Arndt-Eistert Homologation • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Base-Catalyzed Hydration of α,β -Unsaturated Aldehydes and Ketones • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Bucherer-Bergs Reaction • Carbonation of Organometallics • Carboxylate Salt Formation • Carboxylic Acids React with Alcohols to Form Esters • Chan-Lam Coupling Reaction • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Clemmensen Reduction • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Complex Metal Hydride Reductions • Conjugated Enone Takes Part in 1,4-Additions • Conversion of Amino with Nitro • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Cyanohydrins can be Convert to Carbonyl Compounds under Basic Conditions • Decarboxylation of 3-Ketoacids Yields Ketones • Decarboxylation of Substituted Propanedioic • Deoxygenation of the Carbonyl Group • Deprotection of Cbz-Amino Acids • Deprotonation of a Carbonyl Compound at the α -Carbon • Deprotonation of Methylbenzene • Diorganocuprates Convert Acyl Chlorides into Ketones • Directing Electron-Donating Effects of Alkyl • Dithioacetal Formation • Electrophilic Chloromethylation of Polystyrene • Enamines Can Be Used to Prepare Alkylated Aldehydes • Enol-Keto Equilibration • Enolate Ions Are Protonated to Form ketones • Esters Hydrolyze to Carboxylic Acids and Alcohols • Exclusive 1,4-Addition of a Lithium Organocuprate • Fischer Indole Synthesis • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Furan Hydrolyzes to Dicarbonyl Compounds • Geminal Diols and Acetals Can Be Hydrolyzed to Carbonyl Compounds • Grignard Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Benzene • Hantzsch Pyridine Synthesis • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Henry Nitroaldol Reaction • HIO4 Oxidatively Degrades Vicinal Diols to Give Carbonyl Derivatives • Hofmann Rearrangement • Horner-Wadsworth-Emmons Reaction • Hunsdiecker-Borodin Reaction • Hydration of the Carbonyl Group • Hydride Reductions • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydrogenation by Palladium on Carbon Gives the Saturated Carbonyl Compound • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Isomerization of β, γ -Unsaturated Carbonyl Compounds • Ketone Synthesis from Nitriles • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Lawesson's Reagent • Leuckart-Wallach Reaction • Lithium Organocuprate may Add to the α ,β -Unsaturated Carbonyl Function in 1,4-Fashion • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mercury Ions Catalyze Alkynes to Ketones • Michael Addition • Nitration of Benzene • Nitriles Hydrolyze to Carboxylic Acids • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alcohols to Carbonyl Compounds • Oxidation of Aldehydes Furnishes Carboxylic Acids • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Oxidation of Primary Alcohols Furnishes Carboxylic Acids • Passerini Reaction • Paternò-Büchi Reaction • Peptide Bond Formation with DCC • Periodic Acid Degradation of Sugars • Petasis Reaction • Peterson Olefination • Phenylhydrazone and Phenylosazone Formation • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Carboxylic Acids • Prins Reaction • Pyrroles, Furans, and Thiophenes are Prepared from γ-Dicarbonyl Compounds • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Reduction of an Amide to an Amine • Reduction of an Amide to an Amine • Reduction of Carboxylic Acids by LiAlH4 • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reductive Amination • Reductive Amination • Reductive Removal of a Diazonium Group • Reformatsky Reaction • Reverse Sulfonation——Hydrolysis • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Strecker Synthesis • Sulfonation of Benzene • Tebbe Olefination • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Conversion of Carboxylic Acids into Acyl Halides • The Nitro Group Conver to the Amino Function • The Reaction of Alkynyl Anions with Carbonyl Derivatives • The Wittig Reaction • Thiazolium Salt Catalysis in Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Ugi Reaction • Use 1,3-dithiane to Prepare of α-Hydroxyketones • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction
Historical Records

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Amides

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Benzoxazoles

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