Home Cart 0 Sign in  

[ CAS No. 58022-21-2 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 58022-21-2
Chemical Structure| 58022-21-2
Structure of 58022-21-2 *Storage: {[proInfo.prStorage]}

Quality Control of [ 58022-21-2 ]

Related Doc. of [ 58022-21-2 ]

SDS
Alternatived Products of [ 58022-21-2 ]
Alternatived Products of [ 58022-21-2 ]

Product Details of [ 58022-21-2 ]

CAS No. :58022-21-2MDL No. :MFCD08062665
Formula : C11H9NO Boiling Point : 314.568°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :171.20Pubchem ID :13157214
Synonyms :

Computed Properties of [ 58022-21-2 ]

TPSA : 30 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.09 Rotatable Bond Count : 1

Safety of [ 58022-21-2 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 58022-21-2 ]

  • Upstream synthesis route of [ 58022-21-2 ]
  • Downstream synthetic route of [ 58022-21-2 ]

[ 58022-21-2 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 119-65-3 ]
  • [ 127-17-3 ]
  • [ 58022-21-2 ]
YieldReaction ConditionsOperation in experiment
76% With ammonium peroxydisulfate; [Ir(2-(2,4-difluorophenyl)-5-methylpyridine)24,4′-di-tert-butyl-2,2′-bipyridine]PF6 In dimethyl sulfoxide at 20℃; for 12 h; Inert atmosphere; Irradiation; Green chemistry General procedure: Heterocycle (0.10mmol, 1 equiv)ammonium persulfate (0.20 mmol, 2equiv),[Ir{dF(CF3ppy)}2(dtbbpy)]PF6 ( 0.2 molpercent),α-keto acids(1.0mmol10equiv)wereplaced in a dry glass tube.Then, anhydrous DMSO1mLwereinjected into the tubeby syringe under a N2 atmosphere.The solution was then stirred at roomtemperatureunder the irradiation of 15W blue LEDs strip for 12h.After completion of thereaction,then saturated Na2CO3solution was added to adjust pH to basic.Thecombined organic layer was washed with brine and then dried overanhydrousNa2SO4.The desired products were obtained in thecorresponding yields afterpurification by flashchromatography on silica gel eluting with petroleum andethylacetate.
70% With dipotassium peroxodisulfate In water at 100℃; Sealed tube General procedure: To a solution of isoquinoline 1a (0.5 mmol) in water (2 mL) was added keto acid 2a (1.25 mmol), followed by K2S2O8 (1.5 mmol). The reaction mixture contained in a sealed tube was heated at 100 °C for 4-6 h. The contents were then cooled in an ice-bath and quenched with the saturated solution of sodium bicarbonate. The resulting mixture was extracted with ethyl acetate (2 × 10 mL) The organic phase was washed with water, dried over anhydrous sodium sulphate and evaporated under diminished pressure to afford the crude residue. The residue was finally purified by column chromatography to obtain the pure acylated product 3a.
Reference: [1] Organic Letters, 2017, vol. 19, # 21, p. 5772 - 5775
[2] Synlett, 2018, vol. 29, # 14, p. 1881 - 1886
[3] Tetrahedron Letters, 2017, vol. 58, # 24, p. 2347 - 2350
  • 2
  • [ 1198-30-7 ]
  • [ 75-16-1 ]
  • [ 58022-21-2 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: at 0℃; for 3 h;
Stage #2: With ammonium chloride In tetrahydrofuran; diethyl ether at 20℃; for 3 h;
A solution of isoquinoline-1-carbonitrile (Intemediate H1) (commercially available from Aldrich) (4.40 g, 28.5 mmol) in THF at 0° C. was treated with methylmagnesium bromide (20 mL, of a 3M soln in ether) for 3 h. (see procedure found in Vacher, B. et al J. Med. Chem. 1998 41, 5070; incorporated herein by reference). The mixture was quenched with a sat. solution of NH4Cl and stirred for 3 h at rt. The aqueous layer was basified with NaOH and extracted with ethyl acetate. The organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The material was purified by chromatography on silica gel with 10percent ethyl acetate: hexane to give 1-isoquinolin-1-yl-ethanone (Intermediate H2) 3.65g (75percent). A mixture of 4-iodo-1-tritylimidazole (commercially available) (15.5 g, 35.4 mmol) in dichloromethane (80 mL) at 20° C. was treated with ethyl magnesium bromide (12.0 mL, 36 mmol, 3M in ether) and allowed to react for 1 h. A solution of 1-isoquinolin-1-yl-ethanone (Intermediate H2) (3.65 g, 21.3 mmol) in dichloromethane (20 mL) was added via addition funnel at 20° C. and stirred for 16 h. The mixture was quenched with sat. ammonium chloride (100 mL) and diluted with dichloromethane. The residue was isolated in an aqueous workup. The product was extracted with CH2Cl2 and purified by chromatography on silica gel with 5percent NH3-MeOH: CH2Cl2 to give 1-isoquinolin-1-yl-1-(1-trityl-1H-imidazol-4-yl)-ethanol (Intermediate H3) as a solid. 1-Isoquinolin-1-yl-1-(1-trityl-1H-imidazol-4-yl)-ethanol (Intermediate H3) was subjected to TFA: trifluoroacetic acid, Pd/C under hydrogen similar to the catalytic reduction procedure of Method D to remove the trityl group and produced 1-1H-imidazol-4-yl)-isoquinolin-1-yl ethanol (Intermediate H4). 1-1H-Imidazol-4-yl)-isoquinolin-1-yl ethanol (Intermediate H4). (21 mmol) in dichloromethane (100 mL) was treated with triethylamine (24.0 mL, 172 mmol) at 0° C. Methanesulfonyl chloride (6.1 mL, 75 mmol) was added via syringe and the mixture was stirred for 2 h. The mixture was subjected to an aqueous work-up. The crude material was purified by chromatography on silica gel with 20percent EtOAc: hexane to 5percent NH3-MeOH: dichloromethane to give 1-[1-(1-methanesulfonyl-1H-imidazol-4-yl)-vinyl]-isoquinoline (Intermediate H5) 3 g. 1-[1-(1-Methanesulfonyl-1H-imidazol-4-yl)-vinyl]-isoquinoline (Intermediate H5) was subjected to the catalytic reduction procedure found in Method D to produce 1-[1-(1-methanesulfonyl-1H-imidazol-4-yl)-ethyl]-isoquinoline (Intermediate H6). Methanesulfonyl-1H-imidazol-4-yl)-ethyl]-isoquinoline (Intermediate H6) in ethanol and 2M HCl was heated at reflux for 18 h. The mixture was cooled to rt and basified with NaOH solid. The aqueous layer was extracted with isopropanol:chloroform (3:1). The organic fractions were dried over MgSO4, filtered and concentrated onto silica gel. The product, 1-[1-(1H-imidazol-4-yl)-ethyl]-isoquinoline (Intermediate H7) was eluted from a column of silica gel with 3 to 5percent NH3-MeOH: CH2Cl2. 1-[1-(1H-Imidazol-4-yl)-ethyl]-isoquinoline (Intermediate H7) was subjected to the appropriate process steps in Method A to produce 4-(1-isoquinolin-1-yl-ethyl)-1,3-dihydro-imidazole-2-thione (Compound 13) 1H NMR (300 MHz, DMSO-d6): δ11.9 (s, 1H), 11.6 (s, 1H), 8.42 (dd, J=5.4, 2.7 Hz, 1H), 8.31 (d, J=8.1 Hz, 1H), 7.96 (d, J=8.1 Hz, 1H), 7.78-7.64 (m, 3H), 6.40 (s, 1H), 5.0 (q, J=6.9 Hz, 1H), 1.59 (d, J=6.9 Hz, 3H).
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2393 - 2412
[2] Patent: US2006/69143, 2006, A1, . Location in patent: Page/Page column 22-23
  • 3
  • [ 866328-99-6 ]
  • [ 676-58-4 ]
  • [ 58022-21-2 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: at 0℃; for 1.16667 h;
Stage #2: With water; ammonium chloride In tetrahydrofuran
Methyl magnesium chloride (12.3 mL of 3.0M THF) was added to a 0 0C solution of amide a (4.0 g, 18.5 mmol) and THF (40 mL). After 30 min at 0 0C, the cooling bath was removed for 40 min. The reaction was poured into cold saturated NH4Cl (200 mL), and extracted with EtOAc (3 x 50 mL). The combined organic phases were washed with water, brine, dried (Na2SO4), and concentrated to yield 3.15 g (100percent) of ketone b as a colorless oil.
Reference: [1] Patent: WO2006/69063, 2006, A1, . Location in patent: Page/Page column 109
  • 4
  • [ 1198-30-7 ]
  • [ 917-64-6 ]
  • [ 58022-21-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 1997, vol. 32, # 5, p. 397 - 408
[2] Chemische Berichte, 1913, vol. 46, p. 2931
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 12, p. 738
  • 5
  • [ 1198-30-7 ]
  • [ 58022-21-2 ]
YieldReaction ConditionsOperation in experiment
62% With methylmagnesium bromide In tetrahydrofuran Example 232
4-Amino-6-chloro-2-(1-(1-isoquinolyl)ethyl)thio-pyrimidine (Cpd #232)
Methyl magnesium bromide in ether (8.1 ml, 24.3 mmole) is dissolved in 16 ml tetrahydrofuran in an oven dried 100 ml two neck round bottom flask under nitrogen.
The solution is cooled to 0° C., is diluted with 8 ml diethyl ether, and is treated with 1-isoquinoline carbonitrile (3.0 g, 19.5 mmole).
The reaction is warmed to reflux for one hour, is cooled to 0° C., and is quenched with 20 ml 6 M hydrochloric acid.
The reaction mixture is warmed to 50° C. for two hours, is cooled, and is poured into 75 ml 2N sodium hydroxide.
The mixture is extracted with 3*80 ml ethyl acetate and the combined organics are dried over potassium carbonate.
The dried organics are concentrated in vacuo to a crude amber oil.
The crude material is chromatographed over 150 g silica gel (230-400 mesh), eluding with 10percent acetone/hexane, while collecting 22 ml fractions.
Fractions 16-26 are combined and concentrated to provide 2.1 g (62percent) of 1-acetylisoquinoline.
H-NMR (CDCl3, TMS): δ 2.87 (s,3), 7.64-7.73 (m, 2), 7.80 (d, J=5.5 Hz, 1), 7.83-7.88 (m, 1), 8.58 (d, J=5.5 Hz, 1), 8.94-8.98 (m, 1) ppm. 13 C-NMR (CDCl3): δ 28.6; 124.6; 125.7; 126.9; 127.0; 129.1; 130.3; 137.0; 141.0; 152.8; 202.7 ppm. TLC (silica gel-60, F-254): Rf =0.45, 20percent acetone/hexane.
Infrared (ν max, liquid): 3054, 1694, 1582, 1358, 1239, 1133, 940, 833, 750 cm-1.
Mass Spectrum, [M/Z](relative intensity): [171](63). Analysis: Calculated for C11 H9 NO: C, 77.17; H,5.30; N,8.18. Found: C, 77.09; H,5.33; N,8.10.
Reference: [1] Patent: US6043248, 2000, A,
  • 6
  • [ 111-34-2 ]
  • [ 123172-86-1 ]
  • [ 58022-21-2 ]
Reference: [1] Tetrahedron, 2001, vol. 57, # 13, p. 2507 - 2514
  • 7
  • [ 97674-02-7 ]
  • [ 123172-86-1 ]
  • [ 58022-21-2 ]
Reference: [1] Tetrahedron, 2001, vol. 57, # 13, p. 2507 - 2514
  • 8
  • [ 86520-96-9 ]
  • [ 58022-21-2 ]
Reference: [1] Synthesis, 1984, # 3, p. 245 - 247
  • 9
  • [ 119-65-3 ]
  • [ 75-07-0 ]
  • [ 58022-21-2 ]
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1991, vol. 27, # 10, p. 1072 - 1075[2] Khimiya Geterotsiklicheskikh Soedinenii, 1991, vol. 27, # 10, p. 1340 - 1343
  • 10
  • [ 119-65-3 ]
  • [ 64-17-5 ]
  • [ 58022-21-2 ]
Reference: [1] Russian Journal of Organic Chemistry, 2010, vol. 46, # 9, p. 1399 - 1402
  • 11
  • [ 29924-67-2 ]
  • [ 58022-21-2 ]
Reference: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 660,663
[2] Chemische Berichte, 1975, vol. 108, p. 3794,3797
  • 12
  • [ 7742-73-6 ]
  • [ 58022-21-2 ]
Reference: [1] Tetrahedron, 2001, vol. 57, # 13, p. 2507 - 2514
  • 13
  • [ 119-65-3 ]
  • [ 58022-21-2 ]
Reference: [1] Journal of the American Chemical Society, 1945, vol. 67, p. 1268
[2] Journal of the American Chemical Society, 1945, vol. 67, p. 1268
  • 14
  • [ 486-73-7 ]
  • [ 58022-21-2 ]
Reference: [1] Journal of the American Chemical Society, 1945, vol. 67, p. 1268
  • 15
  • [ 844-25-7 ]
  • [ 58022-21-2 ]
Reference: [1] Journal of the American Chemical Society, 1945, vol. 67, p. 1268
  • 16
  • [ 50458-78-1 ]
  • [ 141-78-6 ]
  • [ 58022-21-2 ]
Reference: [1] Journal of the American Chemical Society, 1945, vol. 67, p. 1268
  • 17
  • [ 83629-90-7 ]
  • [ 5704-66-5 ]
  • [ 58022-21-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 6, p. 1028 - 1030
  • 18
  • [ 119-65-3 ]
  • [ 56-23-5 ]
  • [ 64-17-5 ]
  • [ 58022-21-2 ]
  • [ 1258282-74-4 ]
Reference: [1] Russian Journal of Organic Chemistry, 2010, vol. 46, # 9, p. 1399 - 1402
  • 19
  • [ 1198-30-7 ]
  • [ 74-88-4 ]
  • [ 58022-21-2 ]
Reference: [1] Chemical & Pharmaceutical Bulletin, 1983, vol. 31, # 2, p. 476 - 481
Historical Records

Related Functional Groups of
[ 58022-21-2 ]

Ketones

Chemical Structure| 59576-26-0

[ 59576-26-0 ]

1-(4-Methylpyridin-2-yl)ethanone

Similarity: 0.88

Chemical Structure| 31170-78-2

[ 31170-78-2 ]

5H-Cyclopenta[b]pyridin-7(6H)-one

Similarity: 0.87

Chemical Structure| 5308-63-4

[ 5308-63-4 ]

1-(5-Methylpyridin-2-yl)ethanone

Similarity: 0.85

Chemical Structure| 22971-32-0

[ 22971-32-0 ]

2-Butyrylpyridine

Similarity: 0.85

Chemical Structure| 137853-21-5

[ 137853-21-5 ]

1-(5-Isopropylpyridin-2-yl)ethanone

Similarity: 0.84

Related Parent Nucleus of
[ 58022-21-2 ]

Isoquinolines

Chemical Structure| 4494-18-2

[ 4494-18-2 ]

Isoquinoline-1-carbaldehyde

Similarity: 0.89

Chemical Structure| 80278-67-7

[ 80278-67-7 ]

Isoquinoline-5-carbaldehyde

Similarity: 0.78

Chemical Structure| 22960-16-3

[ 22960-16-3 ]

Isoquinoline-4-carbaldehyde

Similarity: 0.76

Chemical Structure| 787615-01-4

[ 787615-01-4 ]

Isoquinoline-8-carbaldehyde

Similarity: 0.71

Chemical Structure| 19382-38-8

[ 19382-38-8 ]

Isoquinolin-1-ylmethanamine dihydrochloride

Similarity: 0.71