[ CAS No. 556-08-1 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 556-08-1
Chemical Structure| 556-08-1
Structure of 556-08-1

Quality Control of [ 556-08-1 ]

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Product Details of [ 556-08-1 ]

CAS No. :556-08-1MDL No. :MFCD00002534
Formula :C9H9NO3Boiling Point :439.6°C at 760 mmHg
Linear Structure Formula :HOOCC6H4NHC(O)CH3InChI Key :-
M.W :179.17Pubchem ID :-
Synonyms :

Computed Properties of [ 556-08-1 ]

TPSA : 66.4 H-Bond Acceptor Count : 3
XLogP3 : - H-Bond Donor Count : 2
SP3 : 0.11 Rotatable Bond Count : 2

Safety of [ 556-08-1 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 556-08-1 ]

  • Upstream synthesis route of [ 556-08-1 ]

[ 556-08-1 ] Synthesis Path-Upstream   1~44

  • 1
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YieldReaction ConditionsOperation in experiment
91% With magnesia In neat (no solvent) at 70℃; for 0.58 h; Green chemistry General procedure: In an oven dried round bottomed flask (50 mL) nano-MgO (5.0 molpercent) were added and then alky/aryl amines (5.0 mmol) and aromatic/aliphatic acid (5.0 mmol) was added. After that it was allowed to stir on a pre heated oil bath at 70 °C under aerobic condition till the required time (the progress of the reaction was judged by TLC). After the completion, the reaction mixture was brought to room temperature and ethyl acetate (3 × 10 mL) was added to it and then centrifuged at 3500 rpm to recover the nano catalyst. Having done this, the reaction mixture was washed with water and brine, dried over anhydrous Na2SO4, concentrated in a rotary evaporator and finally the crude product was charged to column chromatography (ethylacetate:hexane (3:7) as an eluent) for purification and wherever necessary the products were recrystallized from hot ethanol.
Reference: [1] Synthetic Communications, 2008, vol. 38, # 7, p. 1028 - 1035
[2] Applied Catalysis A: General, 2013, vol. 456, p. 118 - 125
[3] Green Chemistry, 2012, vol. 14, # 3, p. 847 - 854
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 9, p. 1274 - 1281
[5] Synthetic Communications, 2008, vol. 38, # 17, p. 2929 - 2940
  • 2
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YieldReaction ConditionsOperation in experiment
99%
Stage #1: at 20℃; for 5.00 h;
Stage #2: With hydrogenchloride In water
General procedure: Ac2O (5.7 mL, 60.3 mmol) was added to the solution of 4-amino-benzoic acid (1) (6.86 g, 50.0 mmol) in pyridine (25 mL). The reaction was stirred at room temperature for 5 h. The solvent was removed in vacuo and the residue dispersed in water (100 mL) and acidified to pH 2-3 with concentrated hydrochloric acid. The resulting precipitate was collected by filtration, washed with water (30 mL) and dried to give 4-acetamido-benzoic acid (3) as a pale yellow powder (7.80 g, 99percent).
99% at 20℃; for 5.00 h; Step 1: Ac20 (5.7 ml, 60.3 mmol) was added to the solution of 4-amino-benzoic acid(6.86 g, 50.0 mmol) in pyridine (25 ml). The reaction was stirred at room temperature for 5 h. The solvent was removed in vacuo, and the residue was dispersed in water (100 ml) and acidified to pH 2-3 with concentrated hydrochloric acid. The resulting precipitate was collected by filtration, washed with water (30 ml) and dried to give 4-acetamido-benzoic acid as a pale yellow powder (7.80 g, 99percent).
96% at 55℃; for 2.67 h; 5mol of p-aminobenzoic acid was dissolved in 1.8L mass fraction of 85percent formic acid solution,Control the stirring speed 150rpm, adding 6.5mol of acetic anhydride,Raise the temperature of the solution to 55 ° C,Continue stirring 90min,Distillation under reduced pressure 60kPa 70min,The remaining solution was added 3L mass fraction of 20percent potassium chloride solution,Reduce the temperature of the solution to 15 ° C,Crystal precipitation,filter,With a mass fraction of 15percent sodium bromide solution was washed,The mass fraction of 95percent ether solution was recrystallized,Solid sodium hydroxide dehydration agent dehydration,The final productAcetamidobenzoic acid 859.20g, yield 96percent.
Reference: [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 18, p. 5352 - 5360
[2] Patent: WO2016/57779, 2016, A2. Location in patent: Page/Page column 80
[3] Patent: CN106631858, 2017, A. Location in patent: Paragraph 0006; 0010-0015
[4] Monatshefte fur Chemie, 2007, vol. 138, # 1, p. 95 - 99
[5] Journal of Organic Chemistry, 2012, vol. 77, # 21, p. 9553 - 9561
[6] Journal of Chemical Research, 2010, # 6, p. 354 - 357
[7] Mikrochemie, 1951, vol. 38, p. 358,365
[8] Organic Letters, 2005, vol. 7, # 22, p. 5087 - 5090
[9] Synthesis, 2006, # 19, p. 3316 - 3340
[10] Analytical Biochemistry, 2010, vol. 398, # 2, p. 150 - 160
[11] Journal of the American Society for Mass Spectrometry, 2011, vol. 22, # 9, p. 1515 - 1525
[12] Journal of Molecular Catalysis A: Chemical, 2012, vol. 357, p. 175 - 176
  • 3
  • [ 60-35-5 ]
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YieldReaction ConditionsOperation in experiment
71% at 150℃; for 24.00 h; General procedure: In a typical procedure, a mixture of amine (1 mmol), amide (1 mmol) and 50 mg GO was taken in a round-bottom flask (50 mL) and stirred the mixture using a magnetic stirring bar under open air at 150 °C for 24 h. After the reaction was completed, ethyl acetate (5 mL) was added to the reaction mixture and the catalyst was filtered off. The filtered catalyst was further washed with ethyl acetate and the combined organic layer was evaporated to afford nearly pure product. The residue was further purified by passing through a silica gel columnand eluting with ethyl acetate petroleum ether mixture. All products were characterized by spectral data as well as melting points (for solid compounds).
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 10, p. 899 - 903
  • 4
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Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 340 - 342[2] Zhurnal Organicheskoi Khimii, 1980, vol. 16, # 2, p. 381 - 384
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[4] Kinetics and Catalysis, 2010, vol. 51, # 4, p. 516 - 520
[5] Justus Liebigs Annalen der Chemie, 1921, vol. 423, p. 90,91
[6] Chemische Berichte, 1903, vol. 36, p. 1805
[7] Chemische Berichte, 1885, vol. 18, p. 2942
[8] Chemische Berichte, 1876, vol. 9, p. 1302
[9] Chemische Berichte, 1903, vol. 36, p. 1805
  • 5
  • [ 122-85-0 ]
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Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 4, p. 567 - 569
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  • 6
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Reference: [1] Patent: WO2005/30704, 2005, A1. Location in patent: Page/Page column 188-189
  • 7
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  • 8
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YieldReaction ConditionsOperation in experiment
90% for 0.25 h; Reflux 4-aminobenzoic acid (10) (4 g, 29 mmol) was added to a mixture (1:1)of acetic acid and acetic anhydride (20 mL), stirred, and the reaction mixture was refluxed for 15 min.After the completion of the reaction, the mixture was poured into ice-cooled water and a solid residue was obtained after filtration. The crude was washed three times with 100 mL H2O to remove excessacid. The crude was recrystallized in MeOH, yielding (24) (90percent). IR (KBr): 3340 (NH); 2539 (CH); 1700and 1607 (C=O), cm1. 1H-NMR (400 MHz, DMSO-d6) δ ppm: 2.08 (s, 3H, CH3); 7.68 (d, 2H, C6H4);7.87 (d, 2H, C6H4); 10.24 (s, 1H, NH); 12.68 (s, 1H, COOH). Calculated analysis for C9H9NO3: C, 60.33;H, 5.06; N, 7.82. Found: C, 59.80; H, 4.90; N, 7.52.
Reference: [1] Molecules, 2017, vol. 22, # 11,
  • 9
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Reference: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 17, p. 3401 - 3405
  • 10
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YieldReaction ConditionsOperation in experiment
48% at 75 - 135℃; for 26.00 h; p-acetamidobenzoic acid Starting Materials Ethyl Acetate 0.75 mol Sodium p-aminobenzoate 0.25 mol Sodium methoxide (catalyst) 0.25 mol Ethylene Glycol 150 g. Operating Conditions Pressure Atmospheric Temperature/time regime 75° C./8 h.; then 90° C./2 h.; then 110° C./9 h.; then 120-125° C./2.5 h.; then 135° C./4.5 h. Reaction Progress Monitored by TLC Work-up The reaction mass was allowed to cool to 40° C., transferred to a beaker, diluted with water to a total volume of 500 mL, pH adjusted to 2-3 by addition of 51.3 g. concentrated hydrochloric acid, cooled to 10° C., stirred during 30 min at that temperature and filtered. The filter cake was later drained, washed with 100 mL cold water, drained thoroughly and dried at 60-68° C. to constant weight. 21.5 g. of crys- tals (m.p. 258-259° C. (dec.))were obtained (literature 252° C.) Yield 48percent
Reference: [1] Patent: US2005/27120, 2005, A1. Location in patent: Page/Page column 10
  • 11
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YieldReaction ConditionsOperation in experiment
68% With sodium acetate In acetic acid EXAMPLE 4 STR8 4-Acetylaminobenzoic acid.
A mixture of 4-aminobenzoic acid (Aldrich, 50.0 g, 0.365 mol) and anhydrous sodium acetate (35.0 g, 0.427 mol) in glacial acetic acid (150 mL) was heated to reflux for 15 h.
The mixture was poured into cold water (1 L).
The precipitate was separated by filtration and washed several times with cold water.
The cake was dried in oven at 70° C. and recrystallized from 2:1 water:ethanol to give 43.0 g (68percent) of the title compound as off-white flakes, mp 258° C.
Analysis:
Calculated for C9 H9 NO3: C, 60.32; H, 5.06; N, 7.82 Found: C, 60.51; H, 5.14; N, 7.81
Reference: [1] Patent: US5602277, 1997, A
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