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[ CAS No. 607-32-9 ] {[proInfo.proName]}

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Chemical Structure| 607-32-9
Chemical Structure| 607-32-9
Structure of 607-32-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 607-32-9 ]

CAS No. :607-32-9 MDL No. :MFCD00006905
Formula : C9H6N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :PYGMPFQCCWBTJQ-UHFFFAOYSA-N
M.W : 174.16 Pubchem ID :69085
Synonyms :

Calculated chemistry of [ 607-32-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.56
TPSA : 58.71 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.31
Log Po/w (XLOGP3) : 1.93
Log Po/w (WLOGP) : 2.14
Log Po/w (MLOGP) : 0.39
Log Po/w (SILICOS-IT) : 0.24
Consensus Log Po/w : 1.2

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.64
Solubility : 0.4 mg/ml ; 0.0023 mol/l
Class : Soluble
Log S (Ali) : -2.79
Solubility : 0.284 mg/ml ; 0.00163 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.08
Solubility : 0.146 mg/ml ; 0.000836 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.72

Safety of [ 607-32-9 ]

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 [ 607-32-9 ]

* 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.

  • Upstream synthesis route of [ 607-32-9 ]
  • Downstream synthetic route of [ 607-32-9 ]

[ 607-32-9 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 607-32-9 ]
  • [ 2439-04-5 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1895, vol. <2> 52, p. 10
  • 2
  • [ 607-32-9 ]
  • [ 5430-45-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 15, p. 4972 - 4982
  • 3
  • [ 119-65-3 ]
  • [ 607-32-9 ]
YieldReaction ConditionsOperation in experiment
100% at -15 - 20℃; for 3.3 h; General procedure for the preparation of isoquinolin-5-amine (6)
To a solution of isoquinoline (3.0 g, 23.2 mmol) in 40 mL H2SO4 at -15 °C was added solid KNO3 (2.8 g, 27.8 mmol) in four successive equal portions in 30 min.
The reaction mixture was warmed to room temperature and stirred for 3 h, then poured into ice-water (100 mL).
The pH of the mixture was adjusted to 8-10 with a few drops of ammonia.
The precipitated solids were collected by filtration, washed with methyl-tert-butyl ether (100 mL * 2) and dried to provide 5 (4.0 g, 100percent yield) as a yellow solid.
To compound 5 (2.5 g, 14.4 mmol) in MeOH (50 mL) was added 10percent Pd/C (300 mg), and the mixture was stirred under an atmosphere of hydrogen at room temperature for 3 h.
The mixture was filtered and the filtrate was concentrated under vacuum to give the 6 (0.85 g, 41percent yield) as a tan solid.
94%
Stage #1: at -15 - 20℃;
Stage #2: With ammonium hydroxide In water at 0℃;
To a solution of isoquinoline (120g, 0.929 mol) in H2S04 (1 L) was added KN03 (1 12.6g, 1 .1 15mol) at -15 °C (portionwise). The mixture was stirred at room temperature for 2 hours. TLC (petroleum ether: ethyl acetate= 2: 1 ) showed the reaction was complete. The mixture was added to water (3L) at 0 °C. The mixture was adjusted to pH 8 by the addition of NH4OH and filtered. The filter cake was washed with methyl tertbutyl ether (1 L x 2) and concentrated in vacuo to give 5-nitro- isoquinoline (160g, 94percent) as a yellow solid.
94% at -15 - 20℃; for 2 h; To a solution of isoquinoline (120 g, 0.929 mol) in H2SO4 (10 was added KNO3 (112.6 g, 1.115 mol) at -15° C. (portionwise).
The mixture was stirred at room temperature for 2 hours. TLC (petroleum ether: ethyl acetate=2: 1) showed the reaction was complete.
The mixture was added to water (3 L) at 0° C.
The mixture was adjusted to pH 8 by the addition of NH4OH and filtered.
The filter cake was washed with methyl tertbutyl ether (1 L*2) and concentrated in vacuo to give 5-nitro-isoquinoline (160 g, 94percent) as a yellow solid.
94% at -15 - 20℃; for 2 h; To a solution of isoquinoline (120 g, 0.929 mol) in H2S04 (1 L) was added KNO3 (112.6 g, 1.115 mol) at -15°C (dropwise). The mixture was stirred at room temperature for 2 hours. TLC (petroleum ether: ethyl acetate= 2: 1) showed complete conversion. The mixture was added to water (3 L) at 0°C. The mixture was adjusted to pH 8 by the addition of NH4OH and filtered. The filter cake was washed with methyl tertbutyl ether (1 L x 2) and concentrated under vacuum to give 5-nitro- isoquinoline (160 g, 94percent) as a yellow solid.
66.76% at 0℃; for 2 h; A solution of potassium nitrate (0.04 mol, 4.05 g) in conc. sulphuric acid (23 mL) was added drop-wise to a solution of isoquinoline 1 (0.04 mol, 5 g) in 23 mL of conc. sulphuric acid, with a continual stirring at 0°C for 2 hr. After complete addition, the reaction mixture was poured into crushed ice, and neutralized by ~ 150 mL of ammonia solution. The obtained green precipitate was then filtered off. After drying, a crude pale green solid of 2 was obtained which was purified by recrystallization from toluene, giving dark green needles (4.5 g, 66.76percent).

Reference: [1] Bioorganic Chemistry, 2019, vol. 82, p. 100 - 108
[2] Patent: WO2012/146724, 2012, A2, . Location in patent: Page/Page column 49
[3] Patent: US2014/57942, 2014, A1, . Location in patent: Paragraph 0337-0338
[4] Patent: WO2014/68035, 2014, A1, . Location in patent: Page/Page column 35
[5] Journal of Organic Chemistry, 1986, vol. 51, # 11, p. 2011 - 2021
[6] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 8, p. 1098 - 1109
[7] Organic Letters, 2017, vol. 19, # 1, p. 262 - 265
[8] Archiv der Pharmazie, 2015, vol. 348, # 5, p. 347 - 352
[9] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 8, p. 4617 - 4625
[10] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 22, p. 2623 - 2628
[11] Angewandte Chemie - International Edition, 2018, vol. 57, # 34, p. 11025 - 11029[12] Angew. Chem., 2018, vol. 130, p. 11191 - 11195,5
  • 4
  • [ 27810-64-6 ]
  • [ 607-32-9 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 21, p. 10498 - 10504
  • 5
  • [ 118798-90-6 ]
  • [ 607-32-9 ]
  • [ 107-13-1 ]
Reference: [1] Journal of the American Chemical Society, 1989, vol. 111, # 6, p. 2258 - 2262
  • 6
  • [ 57554-78-6 ]
  • [ 708-14-5 ]
  • [ 607-32-9 ]
  • [ 129881-46-5 ]
  • [ 129881-47-6 ]
Reference: [1] Australian Journal of Chemistry, 1990, vol. 43, # 2, p. 375 - 381
  • 7
  • [ 57554-78-6 ]
  • [ 108-24-7 ]
  • [ 708-14-5 ]
  • [ 607-32-9 ]
  • [ 129881-46-5 ]
  • [ 129881-47-6 ]
Reference: [1] Australian Journal of Chemistry, 1990, vol. 43, # 2, p. 375 - 381
  • 8
  • [ 119-65-3 ]
  • [ 7664-93-9 ]
  • [ 7697-37-2 ]
  • [ 607-32-9 ]
  • [ 7473-12-3 ]
Reference: [1] Journal of the Chemical Society, 1957, p. 2521,2527
  • 9
  • [ 607-32-9 ]
  • [ 58142-46-4 ]
Reference: [1] Monatshefte fuer Chemie, 1893, vol. 14, p. 146
  • 10
  • [ 607-32-9 ]
  • [ 7726-95-6 ]
  • [ 58142-46-4 ]
Reference: [1] Monatshefte fuer Chemie, 1893, vol. 14, p. 146
  • 11
  • [ 607-32-9 ]
  • [ 201150-73-4 ]
Reference: [1] Patent: US2017/112833, 2017, A1,
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