Home Cart 0 Sign in  

[ CAS No. 2486-69-3 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 2486-69-3
Chemical Structure| 2486-69-3
Structure of 2486-69-3 * Storage: {[proInfo.prStorage]}

Quality Control of [ 2486-69-3 ]

Related Doc. of [ 2486-69-3 ]

SDS
Alternatived Products of [ 2486-69-3 ]
Alternatived Products of [ 2486-69-3 ]

Product Details of [ 2486-69-3 ]

CAS No. :2486-69-3 MDL No. :MFCD00016539
Formula : C8H9NO3 Boiling Point : 357.9°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :167.16 g/mol Pubchem ID :288057
Synonyms :

Safety of [ 2486-69-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2486-69-3 ]

  • Upstream synthesis route of [ 2486-69-3 ]
  • Downstream synthetic route of [ 2486-69-3 ]

[ 2486-69-3 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 2486-69-3 ]
  • [ 85740-98-3 ]
Reference: [1] Patent: EP279698, 1990, A3,
  • 2
  • [ 121-34-6 ]
  • [ 2486-69-3 ]
Reference: [1] Patent: US2012/107886, 2012, A1, . Location in patent: Page/Page column 19
[2] Patent: WO2012/75053, 2012, A2, . Location in patent: Page/Page column 83-84
  • 3
  • [ 5081-36-7 ]
  • [ 2486-69-3 ]
Reference: [1] Journal of the Chemical Society, 1921, vol. 119, p. 1431
[2] Journal of the Chemical Society, 1917, vol. 111, p. 232
  • 4
  • [ 619-14-7 ]
  • [ 2486-69-3 ]
Reference: [1] Journal of the Chemical Society, 1917, vol. 111, p. 232
  • 5
  • [ 586-38-9 ]
  • [ 2486-69-3 ]
Reference: [1] Journal of the Chemical Society, 1921, vol. 119, p. 1431
  • 6
  • [ 67-56-1 ]
  • [ 2486-69-3 ]
  • [ 41608-64-4 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: at 70℃; for 24 h;
Stage #2: With sodium hydroxide In water
A solution of 4-amino-3-methoxybenzoic acid (1.5 g, 8.97 mmole) in 15 ml methanol and 4.8 ml sulfuric acid 95-98percent was heated at 70° C. for 24 hrs. Upon completion, the mixture was concentrated down and basified with 2N NaOH solution to pH=8. A solid precipitated out. The suspension was filtered off, solid was washed with water, dried to afford 1.62 g tan solid (56), 100percent yield. 1H-NMR (400 MHz, DMSO)
96% at 80℃; for 3 h; Take a 25ml jar, add 5ml of methanol and 0.5g in order4-amino-3-methoxybenzoic acid, stirring, slowly adding 1 ml of concentrated sulfuric acid,The reaction was refluxed at 80 °C for 3 h. After TLC monitored the reaction, the methanol was decontaminated under vacuum.Saturated sodium carbonate solution was added dropwise to adjust the pH to 9 and 5 ml of dichloromethane was added.The liquid was separated, the organic layer was washed 3 times with saturated sodium chloride, and the aqueous layers were combined.Dichloromethane was extracted twice, the organic layers were combined, and the organic phase was dried over anhydrous sodium sulfate for 1 hour. After the silica gel column, the petroleum ether is separated from the ethyl acetate by 4:1.In other words, 0.52-g methyl 4-amino-3-methoxybenzoate was obtained as an off-white solid.Yield 96percent.
92%
Stage #1: at 0 - 0.7℃; for 1 h;
Stage #2: at 15 - 30℃; for 72 h;
This procedure was adopted from a procedure reported in J. Med. Chem., 54, 7815-7833 (2011). Thionyl chloride (1.78g, 0.015 mol) was added dropwise to methanol (8 mL) at 0 °C over a -25 mm. period keeping the temperature at or below 0.7 °C. The resulting mixture was stirred at 0 °C for 1 hr., then 4-amino-3- methoxybenzoic acid (0.5g, 0,003 mol) [ACROS Chemicals] was added in one portion. The reaction mixture was stirred at ambient temperature for 3 days after which the mixture was concentrated in vacuo. Water (5 mL) was added to the residue and sodium bicarbonate (0.3g, 3.6 mmol) was added in one portion and the mixture was stirred at ambient temperature for 30 min. The mixture was extracted several times with ethyl acetate. The combined organic phase was dried over sodium sulfate, filtered and concentrated in vacuo to give 0.5g (92percent) of methyl 4-amino-3-methoxybenzoate as a brown solid. MS: m/z 182.1 (MH+). 1H NMR (500 MHz, DMSO-d6): 6 3.741 (s, 3H), 3.797 (s, 3H), 5.608 (s, 2H), 6.630 (d, 1H), 7.281 (d, 1H), 7.375 (dd, 1H).
Reference: [1] Patent: US2009/130076, 2009, A1, . Location in patent: Page/Page column 31; 32
[2] Synlett, 2008, # 11, p. 1698 - 1702
[3] Tetrahedron, 2007, vol. 63, # 2, p. 347 - 355
[4] Patent: CN107827776, 2018, A, . Location in patent: Paragraph 0031; 0032; 0033; 0034
[5] Tetrahedron, 2003, vol. 59, # 28, p. 5317 - 5322
[6] Patent: WO2014/165816, 2014, A1, . Location in patent: Page/Page column 79
[7] Journal of Organic Chemistry, 1996, vol. 61, # 17, p. 5804 - 5812
[8] Patent: WO2014/28669, 2014, A1, . Location in patent: Paragraph 00729
[9] Patent: EP2842939, 2015, A1, . Location in patent: Paragraph 1539; 1540
  • 7
  • [ 2486-69-3 ]
  • [ 41608-64-4 ]
YieldReaction ConditionsOperation in experiment
97% With hydrogenchloride In methanol; ethyl acetate (a)
Methyl 4-amino-3-methoxybenzoate.
A stirred solution of 4-amino-3-methoxybenzoic acid (2.50 g, 14.97 mmol) in MeOH saturated with HCl gas was heated at reflux overnight.
The volatiles were removed under reduced pressure and the residue dissolved in EtOAc, washed with saturated NaHCO3 solution, dried over MgSO4 and concentrated under reduced pressure.
The title compound was isolated as a tan solid (97percent).1H NMR (CDCl3) δ: 3.87 (s, 3H), 3.91 (s, 3H), 4.5 (br s, 2H), 6.73 (d, 1H, J = 8.1Hz), 7.46 (s, 1H, with fine splitting). Anal. (C12H11NO3) C, H, N.
Reference: [1] Patent: EP1109560, 2003, B1,
  • 8
  • [ 2486-69-3 ]
  • [ 56256-14-5 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 26, p. 5963 - 5966
[2] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 1518 - 1523
  • 9
  • [ 2486-69-3 ]
  • [ 102362-04-9 ]
Reference: [1] Archiv der Pharmazie, 1990, vol. 323, # 8, p. 507 - 512
  • 10
  • [ 64-17-5 ]
  • [ 2486-69-3 ]
  • [ 73368-41-9 ]
YieldReaction ConditionsOperation in experiment
89.1% Reflux; Inert atmosphere; Cooling; Large scale A 22-L 3-necked RBF equipped with an electrical heating mantle, a thermocouple probe, overhead mechanical stirrer, water-cooled condenser, nitrogen bubbler and addition funnel was charged with 4-amino-3-methoxybenzoic acid (1.0 kg, 5.98 mol, 1.0 equiv.) and ethanol (200 proof) (10.0 L, 10 vol.) to produce a stirrable slurry. Without external cooling, sulfuric acid (1.17 kg, 0.64 L, 12.0 mol, 2.0 equiv.) was then added slowly over 1 h, the slurry initially goes thick, but breaks up and eventually all solids dissolve to form a dark solution. The exothermic addition increased the temperature to -45 °C; additional heating was then applied to bring the solution to reflux and was held at reflux overnight. An HPLC sample was taken and showed -5percent starting benzoic acid remaining. The reflux head was switched to full takeoff and 2.5 L was distilled off. The reaction was cooled to 6 °C in an ice bath and the pH slowly adjusted to 12 by the addition of a solution of sodium hydroxide (50 wt percent, 1.03 kg, 681 ml, 12.9 mol, 2.15 equiv.) in water (3.5 L) keeping the temperature below 20 °C. Following a 30 min. post-stir, an additional quantity of water (4.0 L) was added and stirred at ca. 10 °C for 30 min. The solid were filtered, washed thoroughly with water (4.0 L), and then vacuum dried at 65 °C overnight. The yield of ethyl 4- amino-3-methoxybenzoate was 1.04 kg (89.1percent) as a light brown solid. m.p.= 83-87 °C (DSC); 1H NMR (300 MHz, CDC13) δ 7.56 (1H, dd, J = 7.9, 1.5 Hz), 7.47 (1H, d J=1.5 Hz), 6.66 (1H, d, J= 7.9 Hz), 4.33 (2H, t, J= 7.2 Hz), 4.27 (1H, br s), 3.90 (3H), 1.37 (3H, t, J = 7.2 Hz).
Reference: [1] Journal of the American Chemical Society, 1998, vol. 120, # 14, p. 3332 - 3339
[2] Patent: WO2014/128094, 2014, A1, . Location in patent: Page/Page column 22
[3] European Journal of Medicinal Chemistry, 2007, vol. 42, # 5, p. 567 - 579
[4] Patent: US2009/259049, 2009, A1, . Location in patent: Page/Page column 12
[5] Patent: US2011/86882, 2011, A1, . Location in patent: Page/Page column 27
  • 11
  • [ 2486-69-3 ]
  • [ 73368-41-9 ]
Reference: [1] Patent: US6024937, 2000, A,
  • 12
  • [ 2486-69-3 ]
  • [ 180624-10-6 ]
Reference: [1] Tetrahedron, 2007, vol. 63, # 2, p. 347 - 355
[2] Journal of Organic Chemistry, 1996, vol. 61, # 17, p. 5804 - 5812
Historical Records

Related Functional Groups of
[ 2486-69-3 ]

Carboxylic Acids

Chemical Structure| 2840-26-8

[ 2840-26-8 ]

3-Amino-4-methoxybenzoic acid

Similarity: 0.97

Chemical Structure| 2374-03-0

[ 2374-03-0 ]

4-Amino-3-hydroxybenzoic acid

Similarity: 0.91

Chemical Structure| 74165-74-5

[ 74165-74-5 ]

3-Amino-5-methoxybenzoic acid

Similarity: 0.88

Chemical Structure| 4294-95-5

[ 4294-95-5 ]

2-Amino-4-methoxybenzoic acid

Similarity: 0.87

Chemical Structure| 14206-69-0

[ 14206-69-0 ]

3-Amino-5-hydroxybenzoic acid hydrochloride

Similarity: 0.86

Amines

Chemical Structure| 2840-26-8

[ 2840-26-8 ]

3-Amino-4-methoxybenzoic acid

Similarity: 0.97

Chemical Structure| 73368-41-9

[ 73368-41-9 ]

Ethyl 4-amino-3-methoxybenzoate

Similarity: 0.93

Chemical Structure| 24812-90-6

[ 24812-90-6 ]

Methyl 3-amino-4-methoxybenzoate

Similarity: 0.93

Chemical Structure| 5121-34-6

[ 5121-34-6 ]

Methyl 2-amino-3-methoxybenzoate

Similarity: 0.92

Chemical Structure| 63435-16-5

[ 63435-16-5 ]

Methyl 4-amino-3-hydroxybenzoate

Similarity: 0.92

Aryls

Chemical Structure| 2840-26-8

[ 2840-26-8 ]

3-Amino-4-methoxybenzoic acid

Similarity: 0.97

Chemical Structure| 73368-41-9

[ 73368-41-9 ]

Ethyl 4-amino-3-methoxybenzoate

Similarity: 0.93

Chemical Structure| 24812-90-6

[ 24812-90-6 ]

Methyl 3-amino-4-methoxybenzoate

Similarity: 0.93

Chemical Structure| 5121-34-6

[ 5121-34-6 ]

Methyl 2-amino-3-methoxybenzoate

Similarity: 0.92

Chemical Structure| 63435-16-5

[ 63435-16-5 ]

Methyl 4-amino-3-hydroxybenzoate

Similarity: 0.92

Ethers

Chemical Structure| 2840-26-8

[ 2840-26-8 ]

3-Amino-4-methoxybenzoic acid

Similarity: 0.97

Chemical Structure| 73368-41-9

[ 73368-41-9 ]

Ethyl 4-amino-3-methoxybenzoate

Similarity: 0.93

Chemical Structure| 24812-90-6

[ 24812-90-6 ]

Methyl 3-amino-4-methoxybenzoate

Similarity: 0.93

Chemical Structure| 5121-34-6

[ 5121-34-6 ]

Methyl 2-amino-3-methoxybenzoate

Similarity: 0.92

Chemical Structure| 681465-85-0

[ 681465-85-0 ]

Methyl 4-amino-3-isopropoxybenzoate

Similarity: 0.90