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Chemical Structure| 1571-72-8
Chemical Structure| 1571-72-8
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Product Details of [ 1571-72-8 ]

CAS No. :1571-72-8 MDL No. :MFCD00007697
Formula : C7H7NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :MRBKRZAPGUCWOS-UHFFFAOYSA-N
M.W :153.14 Pubchem ID :65083
Synonyms :
3-Amino-4-hydroxybenzoic acid

Calculated chemistry of [ 1571-72-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 3.0
Molar Refractivity : 39.83
TPSA : 83.55 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) : -6.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.6
Log Po/w (XLOGP3) : 0.5
Log Po/w (WLOGP) : 0.68
Log Po/w (MLOGP) : -0.7
Log Po/w (SILICOS-IT) : 0.02
Consensus Log Po/w : 0.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.44
Solubility : 5.53 mg/ml ; 0.0361 mol/l
Class : Very soluble
Log S (Ali) : -1.82
Solubility : 2.29 mg/ml ; 0.015 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.82
Solubility : 23.1 mg/ml ; 0.151 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 1571-72-8 ]

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 [ 1571-72-8 ]

* 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.

  • Upstream synthesis route of [ 1571-72-8 ]
  • Downstream synthetic route of [ 1571-72-8 ]

[ 1571-72-8 ] Synthesis Path-Upstream   1~28

  • 1
  • [ 149-73-5 ]
  • [ 1571-72-8 ]
  • [ 15112-41-1 ]
YieldReaction ConditionsOperation in experiment
15% at 65℃; for 2 h; benzooxazol-5-carboxylic acid: A mixture of 3-amino-4-hydroxybenzoic acid (500 mg, 3.26 mmol) and trimethyl orthoformate (5 mL) was heated at 65° C. for 2 h under argon. The reaction mixture was cooled to room temperature, filtered and washed with hexanes. The filtrate was concentrated in vacuo to afford the product as a white solid (78 mg, 15percent): 1H NMR (500 MHz, CDCl3): δ 8.57 (d, J=1.5 Hz, 1H), 8.20 (dd, J=8.4, 1.8 Hz, 1H), 8.20 (s, 1H), 7.67 (d, J=9.0 Hz, 1H). MS (M+H, 164).
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8219 - 8248
[2] Patent: US2005/84506, 2005, A1, . Location in patent: Page/Page column 40
[3] Patent: EP1229027, 2002, A1, . Location in patent: Page 18
[4] Patent: EP1229028, 2002, A1, . Location in patent: Page 18
[5] Patent: EP1229037, 2002, A1, . Location in patent: Page 17
  • 2
  • [ 122-51-0 ]
  • [ 1571-72-8 ]
  • [ 15112-41-1 ]
YieldReaction ConditionsOperation in experiment
92% for 3 h; Reflux A mixture of 3-amino-4-hydroxybenzoic acid (8.0 g, 1.0 eq) and 60 mL CH(OEt)3 was heated to reflux for 3 h, and then cooled to rt,. The remaining CH(OEt)3 was removed under reduced pressure to give the desired product (7.8 g, 92percent). 'H NMR (400 MHz, DMSO-c ) δ 13.00 (brs, 1H), 8.85 (s, 1H), 8.30 (s, 1H), 8.03 (d, J = 8.8 Hz, 1H), 7.85 (d, J = 8.8 Hz, 1H).
Reference: [1] Patent: WO2013/97773, 2013, A1, . Location in patent: Paragraph 0268
  • 3
  • [ 64-18-6 ]
  • [ 1571-72-8 ]
  • [ 15112-41-1 ]
Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 2770
  • 4
  • [ 1571-72-8 ]
  • [ 5852-78-8 ]
Reference: [1] ChemMedChem, 2014, vol. 9, # 3, p. 566 - 571
  • 5
  • [ 107-02-8 ]
  • [ 1571-72-8 ]
  • [ 5852-78-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 2, p. 521 - 533
  • 6
  • [ 1445-45-0 ]
  • [ 1571-72-8 ]
  • [ 90322-32-0 ]
YieldReaction ConditionsOperation in experiment
80% at 65℃; for 5 h; 2-methyl benzooxazol-5-carboxylic acid: A mixture of 3-amino-4-hydroxybenzoic acid (1.5 g, 9.79 mmol) and trimethyl orthoacetate (15 mL, large excess) was heated at 65° C. for 5 hrs under argon. The reaction mixture was cooled to room temperature, filtered, washed with hexanes. The filtrate was concentrated in vacuo to afford the product as a yellow solid (1.4 g, 80percent): 1H NMR (500 MHz, CD3OD) δ 8.26 (d, J=1.7 Hz, 1H), 8.07 (dd, J=8.5, 1.6 Hz, 1H), 7.67 (d, J=8.2 Hz, 1H), 2.67 (s, 1H); MS(APCI, M+1): 178.10.
Reference: [1] Patent: US2005/84506, 2005, A1, . Location in patent: Page/Page column 40-41
  • 7
  • [ 108-24-7 ]
  • [ 1571-72-8 ]
  • [ 90322-32-0 ]
Reference: [1] Patent: US2609371, 1949, ,
  • 8
  • [ 67-56-1 ]
  • [ 149-73-5 ]
  • [ 1571-72-8 ]
  • [ 924869-17-0 ]
Reference: [1] Patent: KR101792743, 2017, B1, . Location in patent: Paragraph 0185-0189
  • 9
  • [ 598-21-0 ]
  • [ 1571-72-8 ]
  • [ 134997-87-8 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With sodium hydrogencarbonate In chloroform; water at 0 - 20℃; for 48.83 h;
Stage #2: With hydrogenchloride In chloroform; water
3-amino-4-hydroxybenzoic acid (4.0 g, 26.0 mmol) was dissolved in 168 mL of chloroform. 92 mL of saturated sodium bicarbonate solution was added and the new bi-phase mixture was stirred vigorously and cooled to 0° C. using an ice bath. Bromoacetylbromide (3.42 mL, 39 mmol) was added drop-wise. Fifteen minutes later the solution was removed from the ice bath and maintained at room temperature for 48 hours. HPLC (Eclipse XDB-C18, 4.6.x.250 mm, 5 micron, 1-99percent CH3CN/H2O with 0.1percent trifluoroacetic acid) chromatogram indicated that all of the starting material was gone and a new peak (Rt=3.7 min) had formed. The reaction mixture was quenched using concentrated hydrochloric acid until the solution reached a pH of 2. The organic layer was separated and the aqueous phase was extracted with 100 mL of chloroform. The combined organic layers were treated with 75 mL of 10percent hydrochloric acid solution and separated once again. The organic phase was dried over Na2SO4, filtered and concentrated to give 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylic acid (4.8 g, 24.7 mmol, 95percent) as an off-white amorphous solid. MS (ES) m/e 194 [M+H]+.
Reference: [1] Patent: US2008/21023, 2008, A1, . Location in patent: Page/Page column 122-123
  • 10
  • [ 79-04-9 ]
  • [ 1571-72-8 ]
  • [ 134997-87-8 ]
YieldReaction ConditionsOperation in experiment
74% With potassium carbonate In tetrahydrofuran; water at 20℃; for 3 h; To a solution of 3-amino-4-hydroxybenzoic acid (10 g, 66 mmol) in THF (25 mL) were added potassium carbonate (14.0 g, 100 mmol) and water (50 mL) and chloroacetyl chloride (8.0 mL, 100 mL) was added. The mixture was stirred at room temperature for 3 hrs. Concentrated hydrochloric acid was added to acidify the reaction solution. The precipitated crystals were collected by filtration. The obtained crystals were washed with water and diisopropyl ether and vacuum dried to give the title compound as brown crystals (9.4 g, yield 74percent). H NMR (300 MHz, DMSO-d6) 8 ppm: 4.65 (s, 2 H), 7.00 (d, J = 8.4 Hz, 1 H), 7.48-7. 52 (m, 2 H), 10.87 (s, 1 H), 12.77 (br, 1 H).
Reference: [1] Patent: WO2004/46107, 2004, A1, . Location in patent: Page 209-210
  • 11
  • [ 67-56-1 ]
  • [ 1571-72-8 ]
  • [ 536-25-4 ]
YieldReaction ConditionsOperation in experiment
99% at 0 - 20℃; for 12 h; Heating / reflux A solution (0.2 M) of acetyl chloride (3.0 eq. ) in MeOH was prepared at 0 °C then allowed to warm to 20 °C. 3-amino-4-hydroxybenzoic acid (1.0 eq. ) was added and the mixture was heated under reflux for 12 h then cooled and concentrated in VACUO. The residue was triturated with H20 and dried to afford the title compound (99percent) as a solid. H NMR (300 MHz, DMSO-D6, 300 K) 8 3.83 (s, 3H), 7.15 (d, J 8.5 Hz, 1H), 7.79 (dd, J2. 1, 8. 5 Hz, 1H), 7.93 (d, J 2. 1 Hz, 1H), 11.65 (br s, 1H).
98% at 0 - 20℃; for 24 h; Hydrogen chloride (1.25M in Methanol, lOOmL) was placed in a reactor at 0°C. Then 3- amino-4-hydroxybenzoic acid (5g, 0.032mo1) was added in portions. The reaction mixture was stirred 5 minutes at 0°C and 24 hours at room temperature. The solvent was removed under reduced pressure and the crude was partitioned between ethyl acetate and satu-rated bicarbonate. The organics layer were combined, dried, filtered and the solvent was removed under reduced pressure to obtain the title compound as a solid (5.38g, 98percent), which was used in the next step without further purification.LRMS (m/z): 168 (M+1)+
57% at 55℃; for 48 h; 3-Amino-4-hydroxybenzoic acid (0.40 g, 2.61 mmol) was dissolved in anhydrous methanol (10 ml) and treated with TMSCl (0.75 ml, 5.94 mmol). The mixture was stirred at 55 °C for 2 days. After evaporation of the solvent, the obtained residue was purified by column chromatography on silica gel eluting with ethyl acetate (yield: 0.25 g, 1.50 mmol, 57percent, white solid). 0.20 g of the obtained methyl 3-amino-4-hydroxybenzoate, dissolved in anhydrous THF (10 ml), was mixed with TCDI (0.26 g, 1.46 mmol) under an inert atmosphere. The solution was stirred overnight at room temperature. After evaporation of the solvent the residue was treated with water (15 ml) and extracted with ethyl acetate (3 .x. 15 ml). The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The remaining crude product was recrystallized from ethanol yielding 0.22 g (1.05 mmol, 88percent) of methyl 2-sulfanylbenzo[d]oxazole-5-carboxylate (21) as a brown solid. Mp: 203-205 °C.
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 5, p. 1314 - 1317
[2] Patent: WO2004/87714, 2004, A1, . Location in patent: Page 53
[3] Patent: WO2014/95920, 2014, A1, . Location in patent: Page/Page column 66
[4] European Journal of Organic Chemistry, 2011, # 1, p. 100 - 109
[5] Heterocycles, 2011, vol. 83, # 12, p. 2851 - 2856
[6] MedChemComm, 2014, vol. 5, # 4, p. 474 - 488
[7] European Journal of Medicinal Chemistry, 2004, vol. 39, # 3, p. 291 - 298
[8] European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 4419 - 4429
[9] CrystEngComm, 2011, vol. 13, # 24, p. 7207 - 7211
[10] Justus Liebigs Annalen der Chemie, 1900, vol. 311, p. 55
[11] Patent: DE97333, , ,
[12] Xenobiotica, 1995, vol. 25, # 5, p. 501 - 510
[13] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 14, p. 6724 - 6731
[14] Patent: US2009/176775, 2009, A1, . Location in patent: Page/Page column 29-30
[15] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 14, p. 4001 - 4013
  • 12
  • [ 75-36-5 ]
  • [ 1571-72-8 ]
  • [ 536-25-4 ]
YieldReaction ConditionsOperation in experiment
99% at 0 - 20℃; for 12 h; Heating / reflux A solution (0.2 M) of acetyl chloride (3.0 eq) in MeOH was prepared at 0 °C then allowed to warm to 20 °C. 3-amino-4-hydroxybenzoic acid (1.0 eq) was added and the mixture was heated under reflux for 12 h then cooled and concentrated in vacuo. The residue was triturated with H20 and dried to afford the title compound (99 percent) as a solid. 'H NMR (300 MHz, DMSO-d6) S 3.83 (s, 3H), 7.15 (d, J 8. 5 Hz, 1H), 7.79 (dd, J 2. 1, J 8.5 Hz, 1H), 7.93 (d, J 2.1 Hz, 1H), 11.65 (br s, 1H)
Reference: [1] Patent: WO2005/34941, 2005, A1, . Location in patent: Page/Page column 19
  • 13
  • [ 18107-18-1 ]
  • [ 1571-72-8 ]
  • [ 536-25-4 ]
YieldReaction ConditionsOperation in experiment
51% for 0.5 h; 3-(dimethylamino)-4-hvdroxybenzoic acid: 3-Amino-4-hydroxybenzoic acid (459mg, 3 mmol) was dissolved in methanol (12ml) and toluene (36ml) was added. A 2.0M solution of (trimethylsilyl)diazomethane in hexanes (1.5ml, 3.0 mmol) was added dropwise and the mixture stirred for 0.5h. The reaction mixture was concentrated under vacuum and the residue purified by flash column chromatography on silica to afford methyl 3-amino-4-hydroxybenzoate as a pink solid (254mg, 51percent).A buffer solution at pH 5.5 was prepared by the addition of acetic acid to a 1M aqueous sodium acetate solution. Methyl 3-amino-4-hydroxybenzoate (254mg, 1.5 mmol) was dissolved in a mixture of buffer (1ml) and methanol (2ml). Formaldehyde solution (37percent by weight in water; 0.75ml, lOmmol) was added, the mixture stirred for 15 minutes, and then sodium cyanoborohydride (283mg, 4.5mmol) was added portionwise. The reaction mixture was stirred for an additional 0.5h and then concentrated. The residual oil was partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were washed with water, brine and dried over sodium sulfate. The solvent was removed and the crude product was purified by flash column chromatography on silica to give methyl 3-dimethylamino-4-hydroxybenzoate as a yellow gum (213mg, 73percent).To a solution of methyl 3-dimethylamino-4-hydroxybenzoate (210mg, 1.1 mmol) in 1,4-dioxane (2ml) was added 1 M LiOH (aq) (4mmol). After stirring for 4Oh, the mixture was acidified to pH 2 by addition of 1 M HCI (aq). The mixture was partitioned between water and ethyl acetate, and the aqueous layer was lyophilized to give a mixture of sodium chloride and 3-dimethylamino-4- hydroxybenzoic acid as a brown semi-solid (378mg). The crude material was used in the subsequent reaction.
51% for 0.5 h; 4.14 3-(dimethylamino)-4-hvdroxybenzoic acid; 3-Amino-4-hydroxybenzoic acid (459 mg, 3 mmol) was dissolved in methanol (12 ml) and toluene (36 ml) was added. A 2.0 M solution of (trimethylsilyl)diazomethane in hexanes (1.5 ml, 3.0 mmol) was added dropwise and the mixture stirred for 0.5h. The reaction mixture was concentrated under vacuum and the residue purified by flash column chromatography on silica to afford methyl 3-amino-4-hydroxybenzoate as a pink solid (254 mg, 51 percent).
Reference: [1] Patent: WO2006/64286, 2006, A1, . Location in patent: Page/Page column 98
[2] Patent: WO2007/144379, 2007, A1, . Location in patent: Page/Page column 43
[3] Patent: WO2007/70173, 2007, A2, . Location in patent: Page/Page column 92-93
  • 14
  • [ 1571-72-8 ]
  • [ 536-25-4 ]
Reference: [1] Archiv der Pharmazie, 2008, vol. 341, # 6, p. 386 - 392
  • 15
  • [ 616-82-0 ]
  • [ 1571-72-8 ]
YieldReaction ConditionsOperation in experiment
98% at 0℃; for 1 h; Reflux To tin(II) chloride (207 mg, 1.09 mmol), 12N-HCl (1.5 mL) and 4-hydroxy-3-nitrobenzoic acid (100 mg, 0.55 mmol) were added successively at 0°C, and the reaction mixture was refluxed for 1 h. After addition of water, the reaction mixture was adjusted to pH 1 using 2N NaOH. The precipitates obtained were filtered and washed with water. The filtrate was concentrated in vacuo, and methanol was added to the residue. The formed precipitate was filtered, and the filtrate was concentrated in vacuo. The resulting residue was purified by silica gel column chromatography using methylene chloride and methanol (5:1) as eluent to obtain compound 1 (82 mg, 98percent) as a brown solid [1H NMR (500 MHz, DMSO-d6) δ 11.30 (brs, 1 H), 9.42 (brs, 3 H), 7.79 (s, 1 H), 7.60 (d, 1 H, J = 8.0 Hz), 7.07 (d, 1 H, J = 8.0 Hz)].
98% With hydrogenchloride; tin(ll) chloride In tetrahydrofuran; water at 0℃; for 1 h; Concentrated hydrochloric acid (12N-HCl, 1.5 mL)Tin tailored to 0 (II) chloride (tin (II) chloride, 207 mg, 1.09 mmol)After the addition to the,4-hydroxy-3-nitrobenzoic acid (100 mg, 0.55 mmol)And the mixture was stirred under reflux for 1 hour. Then,Water was added and the pH was adjusted to 1 by addition of 2N-NaOH.The resulting solid was filtered, washed with water, and the filtrate was concentrated under reduced pressure,Methanol was added and filtered again.The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (methylene chloride: methanol = 5: 1) to obtain Compound 57 (82 mg, 98percent) as a brown solid.
95% With palladium on activated charcoal; hydrogen In methanol at 20℃; A mixture of 4-hydroxy-3-nitrobenzoic acid (10 g, 1.0 eq) and 2 g Pd/C in 100 mL MeOH was stirred at rt under H2 (1 atm) overnight, and then filtered. The filtrate was concentrated under reduced pressure to afford the desired product (8.0 g, 95percent). :H NMR (400 MHz, DMSO-c ) δ 10.00 (brs, 1H), 7.19 (s, 1H), 7.07 (d, J = 8.4 Hz, 1H), 6.67 (d, J = 8.4 Hz, 1H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 4, p. 684 - 688
[2] Patent: KR2018/117068, 2018, A, . Location in patent: Paragraph 0084; 0283; 0286; 0288; 0289
[3] Patent: WO2013/97773, 2013, A1, . Location in patent: Paragraph 0267
[4] Chemische Berichte, 1896, vol. 29, p. 1758
[5] Zeitschrift fuer Chemie, 1866, p. 648
[6] Journal of the Chemical Society, 1935, p. 196,199
[7] Journal of Organic Chemistry, 1989, vol. 54, # 15, p. 3740 - 3744
  • 16
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Reference: [1] Journal of the American Chemical Society, 1929, vol. 51, p. 508
  • 17
  • [ 91004-38-5 ]
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Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 6237
  • 18
  • [ 23685-91-8 ]
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Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 2770
  • 19
  • [ 94-26-8 ]
  • [ 1571-72-8 ]
Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 2770
  • 20
  • [ 96-99-1 ]
  • [ 1571-72-8 ]
Reference: [1] Patent: WO2013/97773, 2013, A1,
  • 21
  • [ 99-96-7 ]
  • [ 1571-72-8 ]
Reference: [1] Journal of the Chemical Society, 1935, p. 196,199
[2] Chemische Berichte, 1896, vol. 29, p. 1758
  • 22
  • [ 536-25-4 ]
  • [ 1571-72-8 ]
Reference: [1] Journal of the Society of Chemical Industry, London, 1945, vol. 64, p. 212,214
  • 23
  • [ 13052-92-1 ]
  • [ 1571-72-8 ]
Reference: [1] Chemische Berichte, 1897, vol. 30, p. 991
  • 24
  • [ 99-42-3 ]
  • [ 1571-72-8 ]
Reference: [1] Journal of the Society of Chemical Industry, London, 1945, vol. 64, p. 212,214
  • 25
  • [ 19013-10-6 ]
  • [ 1571-72-8 ]
Reference: [1] Chemische Berichte, 1897, vol. 30, p. 991
  • 26
  • [ 140648-39-1 ]
  • [ 63-74-1 ]
  • [ 1571-72-8 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1992, vol. 57, # 2, p. 268 - 275
  • 27
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  • [ 15126-06-4 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 16, p. 2281 - 2284
  • 28
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  • [ 848133-75-5 ]
Reference: [1] Patent: CN107325049, 2017, A,
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