27655-41-0|5-Cyanoisoquinoline| Ambeed

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Quality Control of [ 27655-41-0 ] Purity: 97% SDS Specification

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Product Details of [ 27655-41-0 ]

CAS No. :	27655-41-0
Formula :	C₁₀H₆N₂
M.W :	154.17
SMILES Code :	C(#N)C1=C2C(=CC=C1)C=NC=C2
MDL No. :	MFCD03109890
InChI Key :	XVJDHUCBVHTPGE-UHFFFAOYSA-N
Pubchem ID :	459770

Safety of [ 27655-41-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 27655-41-0 ]

* 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.

Downstream synthetic route of [ 27655-41-0 ]

[ 27655-41-0 ] Synthesis Path-Downstream 1~35

1
[ 27655-41-0 ]
[ 3389-21-7 ]
[ 111529-99-8 ]

References: [1]Journal of Organic Chemistry,1958,vol. 23,p. 949,953.

2
[ 27655-41-0 ]
[ 927-77-5 ]
1-[5]isoquinolyl-butan-1-one [ No CAS ]

References: [1]Journal of the American Chemical Society,1953,vol. 75,p. 3361,3370.

3
[ 27655-41-0 ]
[ 27810-64-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	With hydrogenchloride; water; In water; at 100℃; for 6h;	Isoquinoline-5-carbonitrile (6 g, 38.62 mmol) obtained in Step (1) above and distilled water (90 mL) were mixed and stirred. The reaction solution was added with concentrated HCl solution (15 mL) and stirred for about 6 hours at 100C. The reaction mixture was cooled to room temperature and adjusted to have a pH value in a range of 5∼6 by adding DIPEA (about 40 mL). The resulting solid mixture was stirred for about 3 hours at room temperature and filtered. The residue was dried in an oven at 50C to obtain the title compound (5.6 g, 84 %). MS (ESI+, m/z): 174 [M+H]+
84%	With hydrogenchloride; water; at 100℃; for 6h;	Isoquinoline-5-carbonitrile (6 g, 38.62 mmol) obtained in Step (1) above and distilled water (90 mL) were mixed and stirred. The reaction solution was added with concentrated HCl solution (15 mL) and stirred for about 6 hours at 100 C. The reaction mixture was cooled to room temperature and adjusted to have a pH value in a range of 5˜6 by adding DIPEA (about 40 mL). The resulting solid mixture was stirred for about 3 hours at room temperature and filtered. The residue was dried in an oven at 50 C. to obtain the title compound (5.6 g, 84%). MS (ESI+, m/z): 174 [M+H]+

References: [1]Patent: EP2876107,2015,A1 .Location in patent: Paragraph 0066.
[2]Patent: US2015/191450,2015,A1 .Location in patent: Paragraph 0127; 0128.
[3]Journal of the American Chemical Society,1939,vol. 61,p. 183.

4
[ 27655-41-0 ]
1-[5]isoquinolyl-ethanone semicarbazone [ No CAS ]

References: [1]Justus Liebigs Annalen der Chemie,1941,vol. 549,p. 238,249.

Yield	Reaction Conditions	Operation in experiment
73%	With [2,2]bipyridinyl; aluminum (III) chloride; bis(acetylacetonate)nickel(II); zinc(II) oxide; In 1,2-dimethoxyethane; at 140℃; for 12h;Sealed tube;	General procedure: No special protection is required. In the air, a magnetic stirrer is added to the clean single-mouth reaction tube.p-Bromoanisole (IIa, 0.2 mmol, 1.0 equiv),Nickel diacetylacetonate (Ni(acac) 2, 0.01 mmol, 5 mol%),Aluminum chloride (AlCl3, 0.02 mmol, 10 mol%),Bipyridine(dipy, 0.04 mmol, 20 mol%),Zinc oxide (ZnO, 0.2 mmol, 1.0 equiv), formamide (1.0 mL)Sealing the reaction tube with ethylene dimethoxide (1,2-dimethoxyethane, 0.5 mL);After reacting at 140 C for 12 hours,Thin layer chromatography analysis showed complete consumption of the crude bromoanisole.Stop heating, cooling; extract, direct wet loading,200-300 mesh silica gel column chromatography,A mixed solvent of ethyl acetate and petroleum ether (1:10) was rinsed.Separating the compound of formula Ia22.6mg,The yield was 85%.
		B. 5 -barboxyisoquinoline A solution of 6.5 g (42 mmol) of the subtitled compound of Preparation 30A in 55 mL of concentrated hydrochloric acid was heated to 155 C. in a sealed tube for 5.5 hours and then was cooled to room temperature, and then reduced to dryness to provide a solid. This solid was redissolved in 300 mL of water, and the resultant solution was adjusted to pH 6 using a dilute ammonium hydroxide solution, resulting in the precipitation of a brown solid. This solid was isolated using filtration, azeotroped with benzene, and then dried at 130 C. under reduced pressure for approximately 3 hours to provide 5.7 g of a fine dark tan powder (m.p. 270-272 C.). Yield: 78%. 1 H NMR (DMSO): δ13.4 (br. s, 1H), 8.69 (d, 1H, J=6.00 Hz), 8.58 (d, 1H, J=4.6 Hz), 8.40 (d, 1H, J=7.37 Hz), 8.36 (d, 1H, J=8.12 Hz), 7.74 (t, 1H, J=7.76); IR (KBr): 3460, 3014, 2930, 2851, 2777, 2405, 1912, 1711, 1622, 1574, 1493, 1427, 1375, 1264, 1211, 1152, 1044.

6
[ 34784-04-8 ]
CuCN [ No CAS ]
[ 27655-41-0 ]

References: [1]Journal of the American Chemical Society,1939,vol. 61,p. 183.

7
sodium salt of/the/ isoquinoline-sulfonic acid-⁽⁵⁾ [ No CAS ]
potassium ferro cyanide [ No CAS ]
[ 27655-41-0 ]

References: [1]Monatshefte fur Chemie,1894,vol. 15,p. 808.

8
sodium salt of/the/ isoquinoline-sulfonic acid-⁽⁸⁾ [ No CAS ]
potassium ferro cyanide [ No CAS ]
[ 27655-41-0 ]

References: [1]Monatshefte fur Chemie,1894,vol. 15,p. 808.

9
Triallylborane [ No CAS ]
[ 27655-41-0 ]
trans-1,3-diallyl-5-cyano-1,2,3,4-tetrahydroisoquinoline [ No CAS ]

References: [1]Journal of Organometallic Chemistry,2002,vol. 657,p. 123 - 128.

10
[ 27655-41-0 ]
[ 102238-27-7 ]

References: [1]Journal of Organic Chemistry,1958,vol. 23,p. 949,953.

11
[ 1125-60-6 ]
[ 27655-41-0 ]

Yield	Reaction Conditions	Operation in experiment
56%	With sodium hydrogencarbonate; sodium nitrite; In hydrogenchloride; water; ethyl acetate; toluene;	A. 5-Cyanoisoquinoline To a cold (0 C.) solution of 10.0 g (61.4 mmol) of 5-aminoisoquinoline in 288 mL of 1.5N hydrochloric acid, was added 15 mL of 5.2M sodium nitrite in water. After approximately 5 minutes, a cool saturated solution of sodium bicarbonate was added to the reaction mixture until the reaction solution tested negative using the iodide and start paper test. The resultant solution was poured into a cold (0-5 C.) biphasic mixture containing 300 ml of toluene and 150 mL of an aqueous solution containing 8.4 g (177 mmol) of sodium cyanide and 7.6 g (85 mmol) of copper cyanide. The resultant reaction mixture was warmed to room temperature, reacted for approximately 1 hour, and then diluted with a mixture of ethyl acetate and water. The resulting layers were separated, and the organic phase was dried over sodium sulfate, filtered, and then reduced to dryness under reduced pressure to provide 5.9 g of a yellow solid. Yield: 56%. 1 H NMR (CDCl3): δ 9.38 (s, 1H), 8.76 (d, J=5.89 Hz, 1H), 8.25 (d, J=8.29 Hz, 1H), 8.13 (d, J=8.30 Hz, 1H), 8.03 (d, J=8.59 Hz, 1H), 7.71 (t, J=7.78 Hz, 1H); IR (KBr): 3433, 3090, 3026, 2924, 2226, 1618, 1574, 1495, 1433, 1373, 1277, 1225, 1034, 829, 766, 714.
56%	With sodium hydrogencarbonate; sodium nitrite; In hydrogenchloride; water; ethyl acetate; toluene;	A. 5-Cyanoisoquinoline To a cold (0 C.) solution of 10.0 g (61.4 mmol) of 5-aminoisoquinoline in 288 mL of 1.5N hydrochloric acid, was added 15 mL of 5.2M sodium nitrite in water. After approximately 5 minutes, a cool saturated solution of sodium bicarbonate was added to the reaction mixture until the reaction solution tested negative using the iodide and starch paper test. The resultant solution was poured into a cold (0-5 C.) biphasic mixture containing 300 ml of toluene and 150 mL of an aqueous solution containing 8.4 g (177 mmol) of sodium cyanide and 7.6 g (85 mmol) of copper cyanide. The resultant reaction mixture was warmed to room temperature, reacted for approximately 1 hour, and then diluted with a mixture of ethyl acetate and water. The resulting layers were separated, and the organic phase was dried over sodium sulfate, filtered, and then reduced to dryness under reduced pressure to provide 5.9 g of a yellow solid. Yield: 56%. 1 H NMR (CDCl3): δ9.38 (s, 1H), 8.76 (d, J=5.89 Hz, 1H), 8.25 (d, J=8.29 Hz, 1H), 8.13 (d, J=8.30 Hz, 1H), 8.03 (d, J=8.59 Hz, 1H), 7.71 (t, J=7.78 Hz, 1H); IR (KBr): 3433, 3090, 3026, 2924, 2226, 1618, 1574, 1495, 1433, 1373, 1277, 1225, 1034, 829, 766, 714.

References: [1]Patent: US5952343,1999,A .
[2]Patent: US5484926,1996,A .

12
[ 27655-41-0 ]
[ 1192829-62-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxylamine hydrochloride; sodium hydrogencarbonate; In ethanol; at 65℃; for 15h;	5-lsoquinolinecarbonitrile (2g, 13mmol; available from Fulcrum Scientific Product List), hydroxylamine. hydrochloride (7.21 g, 104mmol) and sodium bicarbonate (10.9g, 130mmol), were added to a 0.5L round bottomed flask containing ethanol (250ml). The reaction mixture was heated at 65 0C for 3 hours and stirred for 12 hours. The cooled reaction mixture was evaporated to a smaller volume under reduced pressure and chromatographed over a 4x6 inch silica column eluting with ethanol to provide the title compound as a yellow solid (2.9g).MS: (+ve ion electrospray) m/z 188 [MH+], 1H NMR (400 MHz, CD3OD) δ {inter alia) 9.29(1 H1S), 8.49(1 H,d,J 6.0Hz), 8.22(1 H,d,J 8.4Hz), 8.19(1 H,d,J 6.0Hz), 7.97- 7.91 (1 H,m), 7.79-7.73(1 H, m).

References: [1]Patent: WO2009/133136,2009,A1 .Location in patent: Page/Page column 26.

13
[ 27655-41-0 ]
methyl 1-chloroisoquinoline-5-carboxylate [ No CAS ]