Home Cart 0 Sign in  

[ CAS No. 52986-70-6 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 52986-70-6
Chemical Structure| 52986-70-6
Structure of 52986-70-6 * Storage: {[proInfo.prStorage]}

Quality Control of [ 52986-70-6 ]

Related Doc. of [ 52986-70-6 ]

SDS
Alternatived Products of [ 52986-70-6 ]
Alternatived Products of [ 52986-70-6 ]

Product Details of [ 52986-70-6 ]

CAS No. :52986-70-6 MDL No. :MFCD04114861
Formula : C10H9NO Boiling Point : 295.6°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :159.18 g/mol Pubchem ID :11040978
Synonyms :

Safety of [ 52986-70-6 ]

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 [ 52986-70-6 ]

  • Upstream synthesis route of [ 52986-70-6 ]
  • Downstream synthetic route of [ 52986-70-6 ]

[ 52986-70-6 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 52986-70-6 ]
  • [ 7651-82-3 ]
YieldReaction ConditionsOperation in experiment
82% With aqueous HBr In water (c)
6-Methoxyisoquinoline (16 g, 0.1M) and 48percent aqueous HBr (600 ml) were refluxed together for 6 hours and the mixture was then evaporated to dryness in vacuo.
The residue was dissolved in H2 O and basified with solid Na2 CO3.
The resulting precipitated solid was filtered off and recrystallized from isopropanol to give 6-hydroxyisoquinoline (12 g, 82percent), m.p. 218°-20° C. (lit.* 220° C.).
27%
Stage #1: at 160℃;
Stage #2: at 20℃;
b) ISOQUINOLIN-6-OL Heat a mixture of 6-methoxy-isoquinoline (2.1 g, 13.2 mmol) and pyridine hydrochloride (30 g) in a heavy walled screw cap sealed tube at 160C overnight. Cool to room temperature, add water and concentrated ammonium hydroxide to bring the pH of the mixture to 10-11, extract with ethyl acetate (4 times), wash the combined organic extracts with water (4 times), and concentrate under reduced pressure. Purification by medium pressure liquid chromatography eluting with 0-3percent of 2N NH3/MeOH in dichloromethane afford the title compound (520 mg, 27percent) : 8H (DMSO-d6,400 MHz): 7.09 (s, 1H), 7.19 (dd, 1H, J=9,2 Hz), 7.56 (d, 1H, J = 6 Hz), 7.94 (d, 1H, J = 9 HZ), 8.29 (d, 1H, J = 6 Hz), 9.05 (s, 1H), 10.36 (s, 1H).
27% at 160℃; Heat a mixture of 6-methoxy-isoquinoline (2.1 g, 13.2 mmol) and pyridine hydrochloride (30 g) in a heavy walled screw cap sealed tube at 160°C overnight. Cool to room temperature, add water and concentrated ammonium hydroxide to bring the pH of the mixture to 10-11, extract with ethyl acetate (4 times), wash the combined organic extracts with water (4 times), and concentrate under reduced pressure. Purification by medium pressure liquid chromatography eluting with 0-3percent of 2N NH3/MeOH in dichloromethane afford the title compound (520 mg, 27percent) : No.H (DMSO-d6,400 MHz) : 7.09 (s, 1H), 7.19 (dd, 1H, J = 9, 2H2), 7.56 (d, 1H, J = 6 Hz), 7.94 (d, 1H, J = 9 HZ), 8.29 (d, 1H, J = 6 Hz), 9.05 (s, 1H), 10.36 (s, 1H)
Reference: [1] Patent: US4812573, 1989, A,
[2] Patent: WO2004/43904, 2004, A1, . Location in patent: Page 59
[3] Patent: WO2004/43931, 2004, A1, . Location in patent: Page 36-37
[4] Journal of the American Chemical Society, 1947, vol. 69, p. 1944
[5] European Journal of Organic Chemistry, 2003, # 9, p. 1681 - 1686
[6] Patent: WO2004/43903, 2004, A1, . Location in patent: Page 63
[7] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 4, p. 1084 - 1088
  • 2
  • [ 112435-06-0 ]
  • [ 52986-70-6 ]
YieldReaction ConditionsOperation in experiment
45%
Stage #1: With titanium tetrachloride In dichloromethaneHeating / reflux
Stage #2: With water In dichloromethane; water at 20℃;
The material obtained from Step B (15) was dissolved in CH2CI2 (200 mL) and cooled to O0C. Then, Titaniumtetrachloride (86.0 g, 453 mmol) was added and the solution was refluxed overnight. The reaction mixture was allowed to cool down at room temperature. Then, a solution of NaOH (73 g) in water (500 mL) was added and the mixture was shaken for 10 min. The precipitate OfTiO2 was filtered off, and the filtrate extracted with 3N HCl. The pH of the aqueous layer was adjusted to 10 with NaOH. The product was extracted with CH2Cl2, dried (Na2SO4) and evaporated to give 5.32 g EPO <DP n="77"/>(45percent) of the target product 16, which was used without further purification in the next step: m/z = 160 (M+H)+.
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 19, p. 3344 - 3346
[2] Patent: WO2007/14921, 2007, A1, . Location in patent: Page/Page column 74-75
  • 3
  • [ 42923-77-3 ]
  • [ 52986-70-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 16, p. 3045 - 3053
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1993, vol. 32, # 12, p. 1209 - 1213
[3] Organometallics, 2018, vol. 37, # 4, p. 584 - 591
[4] Patent: US4812573, 1989, A,
[5] Journal of the American Chemical Society, 1947, vol. 69, p. 1939,1941
  • 4
  • [ 42923-77-3 ]
  • [ 52986-70-6 ]
  • [ 14446-29-8 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 14, p. 2358 - 2363
  • 5
  • [ 22246-12-4 ]
  • [ 52986-70-6 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1993, vol. 32, # 12, p. 1209 - 1213
  • 6
  • [ 123-11-5 ]
  • [ 52986-70-6 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 19, p. 3344 - 3346
  • 7
  • [ 52986-70-6 ]
  • [ 42923-77-3 ]
Reference: [1] Biochemical Pharmacology, 1995, vol. 50, # 11, p. 1903 - 1912
  • 8
  • [ 52986-70-6 ]
  • [ 42923-77-3 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 7, p. 3829 - 3839
  • 9
  • [ 52986-70-6 ]
  • [ 26829-43-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 1, p. 97 - 101
Historical Records

Related Functional Groups of
[ 52986-70-6 ]

Ethers

Chemical Structure| 90806-58-9

[ 90806-58-9 ]

5-Methoxyisoquinoline

Similarity: 0.91

Chemical Structure| 14446-31-2

[ 14446-31-2 ]

6-Methoxy-3-methylisoquinoline

Similarity: 0.89

Chemical Structure| 1418117-87-9

[ 1418117-87-9 ]

5-Methoxyisoquinoline hydrochloride

Similarity: 0.89

Chemical Structure| 783-08-4

[ 783-08-4 ]

N-Benzylidene-4-methoxyaniline

Similarity: 0.78

Chemical Structure| 49826-70-2

[ 49826-70-2 ]

4-(Benzyloxy)pyridine

Similarity: 0.77

Related Parent Nucleus of
[ 52986-70-6 ]

Isoquinolines

Chemical Structure| 7651-82-3

[ 7651-82-3 ]

Isoquinolin-6-ol

Similarity: 0.92

Chemical Structure| 7651-83-4

[ 7651-83-4 ]

Isoquinolin-7-ol

Similarity: 0.92

Chemical Structure| 90806-58-9

[ 90806-58-9 ]

5-Methoxyisoquinoline

Similarity: 0.91

Chemical Structure| 14446-31-2

[ 14446-31-2 ]

6-Methoxy-3-methylisoquinoline

Similarity: 0.89

Chemical Structure| 1418117-87-9

[ 1418117-87-9 ]

5-Methoxyisoquinoline hydrochloride

Similarity: 0.89