[ CAS No. 27655-41-0 ]

Name: 27655-41-0|5-Cyanoisoquinoline|97%
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Product Details of [ 27655-41-0 ]

CAS No. :	27655-41-0	MDL No. :	MFCD03109890
Formula :	C₁₀H₆N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XVJDHUCBVHTPGE-UHFFFAOYSA-N
M.W :	154.17	Pubchem ID :	459770
Synonyms :

Safety of [ 27655-41-0 ]

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 [ 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.

Upstream synthesis route of [ 27655-41-0 ]
Downstream synthetic route of [ 27655-41-0 ]

[ 27655-41-0 ] Synthesis Path-Upstream 1~1

1
[ 27655-41-0 ]
[ 27810-64-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	With hydrogenchloride; water In water at 100℃; for 6 h;	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 percent). MS (ESI⁺, m/z): 174 [M+H]⁺
84%	at 100℃; for 6 h;	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, 84percent). MS (ESI⁺, m/z): 174 [M+H]⁺

Reference： [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

[ 27655-41-0 ] Synthesis Path-Downstream 1~69

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

Reference： [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 ]

Reference： [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]+

Reference： [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

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.

5
[ 34784-04-8 ]
CuCN [ No CAS ]
[ 27655-41-0 ]

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

6
sodium salt of/the/ isoquinoline-sulfonic acid-⁽⁵⁾ [ No CAS ]
potassium ferro cyanide [ No CAS ]
[ 27655-41-0 ]

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

7
sodium salt of/the/ isoquinoline-sulfonic acid-⁽⁸⁾ [ No CAS ]
potassium ferro cyanide [ No CAS ]
[ 27655-41-0 ]

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

8
[ 27655-41-0 ]
[ 102238-27-7 ]

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

9
[ 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.

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

10
[ 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).

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

11
[ 27655-41-0 ]
methyl 1-chloroisoquinoline-5-carboxylate [ No CAS ]

Reference： [1]Patent: EP2876107,2015,A1
[2]Patent: US2015/191450,2015,A1

12
[ 27655-41-0 ]
methyl 1-((5-methoxypyridin-2-yl)amino)isoquinoline-5-carboxylate [ No CAS ]

Reference： [1]Patent: EP2876107,2015,A1
[2]Patent: US2015/191450,2015,A1

13
[ 27655-41-0 ]
[ 16675-59-5 ]

Reference： [1]Patent: EP2876107,2015,A1
[2]Patent: US2015/191450,2015,A1

14
[ 27655-41-0 ]
5-(methoxycarbonyl)isoquinoline 2-oxide [ No CAS ]

Reference： [1]Patent: EP2876107,2015,A1
[2]Patent: US2015/191450,2015,A1

15
[ 27655-41-0 ]
methyl 1-(t-butylamino)isoquinoline-5-carboxylate [ No CAS ]

Reference： [1]Patent: EP2876107,2015,A1
[2]Patent: US2015/191450,2015,A1

16
[ 27655-41-0 ]
1-(t-butylamino)isoquinoline-5-carboxylic acid [ No CAS ]

Reference： [1]Patent: EP2876107,2015,A1
[2]Patent: US2015/191450,2015,A1

17
[ 27655-41-0 ]
1-amino-N-(2-methyl-5-(3-(trifluoromethyl)benzamido)phenyl)isoquinoline-5-carboxamide [ No CAS ]

Reference： [1]Patent: EP2876107,2015,A1
[2]Patent: US2015/191450,2015,A1

18
[ 27655-41-0 ]
1-(t-butylamino)-N-(2-methyl-5-(3-(trifluoromethyl)benzamido)phenyl)isoquinoline-5-carboxamide [ No CAS ]

Reference： [1]Patent: EP2876107,2015,A1
[2]Patent: US2015/191450,2015,A1

19
[ 557-21-1 ]
[ 34784-04-8 ]
[ 27655-41-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 100℃; for 4h;	5-Bromoisoquinoline (8 g, 38.65 mmol) and dimethyl formamide (100 mL) were mixed and stirred. The reaction solution was added with Zn(CN)2 (2.72 g, 23.19 mmol) and Ph(PPH)4 (1.78 g, 1.55 mmol), followed by stirring for about 4 hours at 100C. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and washed with a saturated aqueous sodium bicarbonate solution and saline. The resulting organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the title compound (5.8 g, 97 %). 1H-NMR Spectrum (300 MHz, DMSO-d6): δ 9.45 (s, 1H), 8.72 (d, 1H), 8.50 (d, 1H), 8.39 (d, 1H), 7.94 (d, 1H), 7.85 (t, 1H). MS (ESI+, m/z): 155 [M+H]+
97%	With Ph(PPH)4; In N,N-dimethyl-formamide; at 100℃; for 4h;	5-Bromoisoquinoline (8 g, 38.65 mmol) and dimethyl formamide (100 mL) were mixed and stirred. The reaction solution was added with Zn(CN)2 (2.72 g, 23.19 mmol) and Ph(PPH)4 (1.78 g, 1.55 mmol), followed by stirring for about 4 hours at 100 C. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and washed with a saturated aqueous sodium bicarbonate solution and saline. The resulting organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the title compound (5.8 g, 97%). 1H-NMR Spectrum (300 MHz, DMSO-d6): δ 9.45 (s, 1H), 8.72 (d, 1H), 8.50 (d, 1H), 8.39 (d, 1H), 7.94 (d, 1H), 7.85 (t, 1H). MS (ESI+, m/z): 155 [M+H]+
24 g	With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 100℃; for 2h;Inert atmosphere;	To a solution (degassed with nitrogen) of intermediate 2 (45 g, 216 mmoles) in DMF (450 mL) there are added Zn(CN)2 (30 g) and Pd(PPh3)4(9.8 g). The mixture is heated at 100 C. for 2 hours. After return to ambient temperature, the mixture is taken up in AcOEt (200 mL) and water (2 L). The mixture is brought to pH>8 by addition of a 20% aqueous NaOH solution. After addition of AcOEt (200 mL), the organic phase is recovered by decantation, filtered over Celite, washed with a saturated aqueous NaCl solution and then dried over MgSO4 before being concentrated in vacuo. The solid is ground and dried in vacuo and taken up in a 1N aqueous HCl solution (1 L), and the acidic aqueous phase is washed with AcOEt and then treated with a 20% aqueous NaOH solution, the precipitate that forms is collected and dissolved in methylene chloride. The solution is dried over MgSO4, and evaporation in vacuo yields intermediate 653 in the form of a beige solid (24 g). 1H NMR (400 MHz; DMSO-d6): δ 9.53 (s, 1H), 8.76 (d, 1H), 8.54 (d, 1H), 8.45 (d, 1H), 7.96 (d, 1H), 7.87 (t, 1H). IR (cm-1): 2226.

Reference： [1]Patent: EP2876107,2015,A1 .Location in patent: Paragraph 0065
[2]Patent: US2015/191450,2015,A1 .Location in patent: Paragraph 0124-0126
[3]Patent: US2017/137385,2017,A1 .Location in patent: Paragraph 0223; 0224; 0225

20
[ 27655-41-0 ]
1-aminoisoquinoline-5-carboxylic acid hydrochloride [ No CAS ]

Reference： [1]Patent: US2015/191450,2015,A1

21
[ 34784-04-8 ]
[ 27655-41-0 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 860 - 863

22
5-((trimethylsilyl)ethynyl)isoquinoline [ No CAS ]
[ 27655-41-0 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 860 - 863

23
5-ethynylisoquinoline [ No CAS ]
[ 27655-41-0 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 860 - 863

24
[ 27655-41-0 ]
8-chloroisoquinoline-5-carbaldehyde hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; for 20h;Reflux;	To a 37% HCl solution (137 mL) there is added intermediate 653, and the mixture is heated at reflux for 20 h. After return to ambient temperature, the precipitate is collected on a frit, washed with acetone and dried in an oven at 50 C. in vacuo (10-2 mbar). The hydrochloride of intermediate 654 is obtained in the form of a white solid (33 g), which is used in the following step without additional purification. 1H NMR (300 MHz; DMSO-d6): δ 10.00 (s, 1H), 9.20 (d, 1H), 8.00 (m, 3H), 8.10 (t, 1H). IR (cm-1): 1695, 1214

Reference： [1]Patent: US2017/137385,2017,A1 .Location in patent: Paragraph 0226; 0227; 0228

25
[ 27655-41-0 ]
C₁₀H₆ClNO*(x)ClH [ No CAS ]

Reference： [1]Patent: US2017/137385,2017,A1

26
[ 27655-41-0 ]
2,2,2-trifluoro-N-{1-[3-hydroxy-4-(isoquinolin-5-ylcarbonyl)-5-methylphenyl]ethyl}acetamide [ No CAS ]

Reference： [1]Patent: US2017/137385,2017,A1

27
[ 27655-41-0 ]
[ 98-89-5 ]
1-cyclohexyl-5-cyanoisoquinoline [ No CAS ]

Reference： [1]ACS Catalysis,2017,vol. 7,p. 4057 - 4061

28
[ 27655-41-0 ]
[ 89343-06-6 ]
[ 2937-50-0 ]
C₂₅H₃₂N₂O₂Si [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 10715 - 10721

29
[ 110-88-3 ]
[ 27655-41-0 ]
1-(1,3,5-trioxan-2-yl)isoquinoline-5-carbonitrile [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 5752 - 5756

30
[ 27655-41-0 ]
[ 1192829-42-7 ]

Reference： [1]Patent: WO2009/133136,2009,A1

31
[ 27655-41-0 ]
[ 1192829-49-4 ]

Reference： [1]Patent: WO2009/133136,2009,A1

32
[ 27655-41-0 ]
[ 1192829-44-9 ]

Reference： [1]Patent: WO2009/133136,2009,A1

33
[ 27655-41-0 ]
[ 1192829-46-1 ]

Reference： [1]Patent: WO2009/133136,2009,A1

34
[ 27655-41-0 ]
[ 1192829-50-7 ]

Reference： [1]Patent: WO2009/133136,2009,A1

35
[ 27655-41-0 ]
[ 1192829-48-3 ]

Reference： [1]Patent: WO2009/133136,2009,A1

36
[ 27655-41-0 ]
[ 1192829-40-5 ]

Reference： [1]Patent: WO2009/133136,2009,A1

37
[ 27655-41-0 ]
[ 1192829-34-7 ]