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Methyl 3-amino-4-ethylbenzoate
Chemistry
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Amines Esters Benzene Compounds
Alternatived Products of [ 24812-93-9 ]
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Product Details of [ 24812-93-9 ]

CAS No. :24812-93-9 MDL No. :MFCD17276539
Formula : C10H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 179.22 Pubchem ID :-
Synonyms :

Safety of [ 24812-93-9 ]

Signal Word: Class:
Precautionary Statements: UN#:
Hazard Statements: Packing Group:

Application In Synthesis of [ 24812-93-9 ]

* 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 [ 24812-93-9 ]

[ 24812-93-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 24812-93-9 ]
  • [ 201286-95-5 ]
YieldReaction ConditionsOperation in experiment
Reference Example 2-12:Methyl 3-methyl-lH-indazole-6-carboxylateAc2theta (0.579 ml, 6.14 mmol) was added to a stirred mixture of KOAc (361 mg, 3.68 mmol) and methyl 3-amino-4-ethylbenzoate (550mg, 3.07 mmol) in CEtaCI3 (5 ml) and the mixture was stirred at 900C for 2h. KOAc (361 mg, 3.68 mmol), 18-crown-6 ether (81 mg, 0.307 mmol) and isobutylnitrate (719 mg, 6.14 mmol) were added thereto at room temperature and the mixture was further stirred at 900C for 2 h. The reaction mixtuer was diluted with chloroform and H2O, the organic layer was washed with water, brine, and dried over MgSOphi After filteration and evaporation, the residue was diluted with THF (5.00 ml) and MeOH (5.00 ml), and K2CO3 (848 mg, 6.14 mmol) was added thereto at room temperature. After the mixture was stirred for 2h. at room temperature, CHCI3 and H2O was added thereto. The organic layer was washed with H2O, brine, and dried over MgSOphi After filteration and evaporation, the residi was puritied by silicagel column chromatography (hexane / EtOAc) to give intended compound as a pale brown solid.
Reference： [1]Patent: WO2010/2010,2010,A1 .Location in patent: Page/Page column 84-85
  • 2
  • [ 24812-93-9 ]
  • [ 7205-46-1 ]
  • [ 1449668-98-7 ]
YieldReaction ConditionsOperation in experiment
6-Chloro-l-methyl-lH-imidazo[4,5-c]pyridine (1.67 g, 0.01 mol), methyl 3-amino-4- ethylbenzoate (2.15 g, 0.012 mol) and caesium carbonate (4.56 g, 0.014 mol) were stirred together in tert-butanol (20 mL) under N2 for 20 min. Chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2'-4'-6'- tri-i-propyl-l,l'-biphenyl][2-(2-aminoethyl)phenyl] palladium(II) (BrettPhos Palladacycle) (0.079 g, 1 mol%) and 2-dicyclohexylphosphino-2',6'-di-iso-propoxy-l,l'-biphenyl (RuPhos) (0.046 g, 1 mol%) were added and the mixture was refluxed for 5 h. The reaction mixture was evaporated in vacuo and the residue was treated with water and extracted into EtOAc. The organics were dried (MgSO i) and concentrated in vacuo to give an oily solid. The residue was dissolved in methanol and loaded onto a 70 g SCX column which was washed with methanol (150 mL) before eluting the product with 7 N N in methanol : methanol (1 :4). The eluent was concentrated in vacuo and the residue was purified by flash chromatography (DCM to 5% methanol in DCM) to give the desired compound. [00338] NMR delta (ppm)(DMSO-d6): 8.51 (1 Eta, s, ArH), 8.16 (1 H, d, ArH), 8.07 (2 H, d, ArH, NH), 7.58 (1 H, dd, ArH), 7.35 (1 H, d, ArH), 6.83 (1 H, s, ArH), 3.96-3.72 (3 H, m, CH3), 3.72 (3 H, s, CH3), 2.71 (2 H, q, CH2), 1.17 (3 H, t, CH3). [00339] LCMS (1 Ocm ESCI Bicarb MeCN) tR 2.77 (min) m/z 311 (MH+).
Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 00337-00339
  • 3
  • [ 24812-93-9 ]
  • [ 108-24-7 ]
  • [ 201286-95-5 ]
YieldReaction ConditionsOperation in experiment
48% The compound obtained from Preparation Example 86-3 was dissolved in chloroform (50ml), and potassium acetate (6.4g, 65.28mmol) was added thereto. The nixture was cooled to 0. Acetic anhydride (16.7g, 163.2mmol) was added dropwise, and the reaction solution was diluted with chloroform (100ml). After adding dropwise isoamylnitrite (12.8g, 108.8mmol), the solution was stirred for 18 hours under reflux. The solution was cooled to room temperature, distilled under reduced pressure to remove the solvent. The residue was dissolved in dichloromethane and washed with brine, dried over anhydrous magnesium sulfate and filtered. Filtrate was distilled under reduced pressure and the residue was dissolved in tetrahydrofuran (100ml). 6N sodium hydroxide (20ml) was added thereto, and the solution was stirred for 2 hours and then extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. Filtrate was distilled under reduced pressure and separated by column chromatography to obtain the title compound (5.90g, 48%). [1169] NMR:1H-NMR(500HMz, CDCl3); delta 8.18 (s, 1H), 7.82 (d, 1H), 7.70 (d, 1H), 3.96 (s, 3H), 2.61 (s, 3H)
Reference： [1]Patent: WO2014/73904,2014,A1 .Location in patent: Paragraph 1166-1169

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Technical Information

• Acyl Group Substitution • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bouveault-Blanc Reduction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Ester Cleavage • Friedel-Crafts Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Alkylbenzene • Preparation of Amines • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction • Vilsmeier-Haack Reaction
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