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Chemistry
Organic Building Blocks
Aryls
nitrobenzoate
Ethyl 4-(cyclohexylamino)-3-nitrobenzoate
Chemistry
Antibiotic and Antivirus
Organic Building Blocks
Structure
Aryls
Amines Esters Nitroes Tetracycline Benzene Compounds
nitrobenzoate
Alternatived Products of [ 87815-77-8 ]
Product Citations

Product Details of [ 87815-77-8 ]

CAS No. :87815-77-8 MDL No. :MFCD06016735
Formula : C15H20N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :PALYDABJRIWMKF-UHFFFAOYSA-N
M.W : 292.33 Pubchem ID :5298559
Synonyms :

Safety of [ 87815-77-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P301+P312-P330 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 87815-77-8 ]

* 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 [ 87815-77-8 ]

[ 87815-77-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 87815-77-8 ]
  • [ 347174-05-4 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen;palladium(II) hydroxide/carbon; In methanol; under 760.051 Torr; for 72h; The nitro derivative from above (24.28 g, 83 mmol) was hydrogenated (1 atm H2) over 20% Pd(OH)2 on carbon (200 mg) in MeOH (150 mL) for 3 days. The catalyst was removed by filtration and volatiles removed under reduced pressure to give the title diamine (21.72 g, 100% yield) as a dark purple solid.
85% With 10% palladium hydroxide on charcoal; hydrogen; In methanol; at 20℃; for 17h; General procedure B (hydrogenolysis) [0274] The ethyl 4-(substituted-amino)-3-nitrobenzoates (130 mg, 0.445 mmol) were dissolved in MeOH (10 mL) and hydrogenated (H2 gas) over 10% Pd(OH)2 on charcoal (90 mg) for 17 hours at room temperature. The solution was filtered through a pad of celite, and volatiles were removed under vacuum. The residue was purified by flash-column chromatography on silica gel to provide the desired Ferrostatin-1 derivatives. General procedure C (reductive amination reaction) (Abdel-Magid et al., 1996)
With hydrogen;palladium 10% on activated carbon; In methanol; ethyl acetate; under 1551.49 Torr; for 6h; Step 8: 3-Amino-4-cyclohexylamino-benzoic acid ethyl ester (Compound 11); [02281 To a solution of 5.84 g (20 mmol) of Compound 10 in 50 mL ethyl acetate and 30 mL methanol, 100 mg of 10% Pd/C was added, and the mixture was hydrogenated at 30 psi for 6 h. The catalyst was removed by filtration through a pad of Celite, the solvent was evaporated to dryness resulting in a dark purple solid which was recrystallized from ether-hexane. The mother liquid was evaporated, and the resulting solid was suspended in hexane and filtered to give additional yield of Compound 11 [02291 MS: 263.18 (M+H) ; H¹-NMR (CDCL3): No.(PPM) 7.57-7. 54 (dd, 1H, J=8.7 and 2.1 Hz, Ar-H6), 7. 39 (d, 1H, J=2. 1HZ, AR-H2), 6.57 (d, 1H, J=9.0 Hz, Ar- H5), 4.29 (q, 2H, J=7. 2Hz, CH2), 3.32 (M, 1H,-CH=), 2.05 (M, 2H), 1.77 (M, 2H), 1.66 (M, 2H), 1.42-1. 20 (M, 7H);
With hydrogen; cyclohexene;palladium on activated carbon; In ethanol; at 83℃; for 3h; Step 2: 3-Amino-4-cyclohexylaminobenzoic acid, ethyl ester In a 250 mL round bottom flask ethyl 4-(cyclohexylamino)-3-nitrobenzoate (3.01 g, 0.0103 mol) was dissolved in ethanol (40 mL) and 1 gram of 5% palladium on carbon (54.62% water) was added. Cyclohexene (7 mL, 0.07 mol) was then added and the reaction heated at 83 C. for 3 hours. The reaction mixture was filtered through celite and the filter cake washed with ethanol. The combined filtrates were concentrated to give 2.3 g title compound as a brownish tan solid. MS (ESI (+)m/z): 263.11 (M+H+).
With 10 wt% Pd(OH)2 on carbon; hydrogen; In methanol; water; at 20℃; for 17h; General procedure: The ethyl 4-(substituted-amino)-3-nitrobenzoates and derivatives (the nitro compounds 3) (1 equiv.) were dissolved in MeOH (10 mL) and hydrogenated (H2 gas) over 10% Pd(OH)2 on charcoal for 17h at room temperature. The solution was filtered through a pad of celite and volatiles were removed under vacuum. The residue was purified by flash-column chromatography on silica gel, using a mixture of solvent of DCM:MeOH (20:1), to providethe desired AA1-AA8 derivatives (Table 1).

Reference： [1]Patent: US2003/236251,2003,A1 .Location in patent: Page 20
[2]Synthesis,2003,p. 1683 - 1692
[3]Journal of the American Chemical Society,2014,vol. 136,p. 4551 - 4556
[4]Patent: WO2015/84749,2015,A1 .Location in patent: Paragraph 0274; 0280
[5]Patent: WO2005/121132,2005,A1 .Location in patent: Page/Page column 40
[6]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1859 - 1863
[7]Patent: WO2005/12288,2005,A1 .Location in patent: Page/Page column 87; 127
[8]Patent: US2011/152260,2011,A1 .Location in patent: Page/Page column 16
[9]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 5315 - 5320
YieldReaction ConditionsOperation in experiment
80% Step 3 Production of Ethyl 3-amino-4-cyclohexylaminobenzoate Ethyl 4-cyclohexylamino-3-nitrobenzoate (400 g) obtained in the previous step was dissolved in ethyl acetate (1500 ml) and ethyl alcohol (500 ml), and 7.5% palladium carbon (50% wet, 40 g) was added. The mixture was hydrogenated for 7 hr at atmospheric pressure. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. Diisopropyl ether was added to the residue and the precipitated crystals were collected by filtration to give the title compound (289 g, yield 80%). 1H-NMR (300 MHz, CDCl3): 7.57 (1H, dd, J=8.4, 1.9 Hz), 7.41 (1H, d, J=1.9 Hz), 6.59 (1H, d, J=8.4 Hz), 4.30 (2H, q, J=7.1 Hz), 3.40-3.30 (1H, m), 2.18-2.02 (2H, m), 1.88-1.15 (8H, m), 1.35 (3H, t, J=7.1 Hz).
  • 3
  • [ 100-52-7 ]
  • [ 87815-77-8 ]
  • [ 347174-05-4 ]
Reference： [1]Organic Process Research and Development,2012,vol. 16,p. 96 - 101

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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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