37993-76-3|3-Phenylisoquinoline| Ambeed

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Structure of 37993-76-3

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Quality Control of [ 37993-76-3 ] Purity: 95% SDS Specification

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Product Details of [ 37993-76-3 ]

CAS No. :	37993-76-3
Formula :	C₁₅H₁₁N
M.W :	205.25
SMILES Code :	C1(C2=CC=CC=C2)=CC3=C(C=N1)C=CC=C3
MDL No. :	MFCD00179548
InChI Key :	RBJOTRVJJWIIER-UHFFFAOYSA-N
Pubchem ID :	609614

Safety of [ 37993-76-3 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H311-H315-H318
Precautionary Statements:	P280-P305+P351+P338-P312
Class:	8(6.1)
UN#:	2923
Packing Group:	Ⅲ

Application In Synthesis of [ 37993-76-3 ]

* 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 [ 37993-76-3 ]

[ 37993-76-3 ] Synthesis Path-Downstream 1~35

1
[ 59046-72-9 ]
[ 37993-76-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	With 4-aminomethylphenol; silver nitrate; In ethanol; at 80℃;	1 mmol of compound 1a, 1.5 mmol of p-hydroxybenzylamine and 1.0 mmol of silver nitrate were dissolved in ethanol, and the reaction was stirred at 80 C. The reaction was monitored by TLC, the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature. The solvent was removed by steaming under reduced pressure.The residue is subjected to column chromatography to obtain the target product 2a.The yield was 78%
69%	With ammonium hydroxide; In water; at 100℃; for 24h;Green chemistry;	General procedure: 2-(Phenylethynyl)benzaldehyde 1a (62.0 mg, 0.3 mmol) and ammonium hydroxide (1 mL) were added into a sealed tube. The mixture was stirred at 100 oC for 24h. After cooled to room temperature, 5 mL water was added. The mixture was extracted with ethyl acetate(10 mL×2). The combined organic phase was dried over anhydrous Na2SO4 for 1h. Next, the solvent was removed under reduced pressure. The crude product was purified by column chromatography to afford the corresponding isoquinoline 2a.
63%	With 4-aminomethylphenol; silver nitrate; In ethanol; at 80℃; for 12h;	General procedure: To a solution of <strong>[59046-72-9]2-(phenylethynyl)benzaldehyde</strong> 1a (62.0 mg, 0.3 mmol) in EtOH (2 mL) was added 4-hydroxybenyzlamine (36.9 mg, 0.3 mmol) and AgNO3 (51.0 mg, 0.3 mmol). The mixture was stirred at 80 C for 12h. Then the reaction was quenched with water, extracted with DCM, dried with anhydrous Na2SO4. The solvent was removed under reduced pressure to afford crude product. Purification furnished the corresponding isoquinoline 3a.

57%	With ammonium bicarbonate; silver nitrate; In acetonitrile; at 100℃;	1 mmol of compound 3, 3 mmol of ammonium bicarbonate and 0.3 mmol of silver nitrate were dissolved in acetonitrile, 100 C stirring reaction, TLC monitoring reaction process, until the reaction is complete, stop the reaction, the reactantAfter cooling to room temperature, the solvent was removed by distillation under reduced pressure and the residue was subjected to column chromatography to give the target compound of formula I.
49%	With trifluorormethanesulfonic acid; ammonium carbonate; In toluene; at 120℃; for 12h;Inert atmosphere;	The reaction is carried out in a reactor. The reactor is evacuated and replaced with argon.2-alkynylbenzaldehyde 1 (0.3 mmol) and ammonium carbonate (3-fold molar amount of 2-alkynylbenzaldehyde 1) were added,Toluene (3 mL) was then added, trifluoromethanesulfonic acid (10 mmol%) was added, and the reaction was carried out at 120C for 12 hours.After the reaction was completed, the solvent was removed and the solid was dissolved in dichloromethane and subjected to silica gel column chromatography.Isoquinoline 2 derivatives are available.
	With copper(l) iodide; ammonium acetate; In tetrahydrofuran; water; at 50℃; for 2h;Green chemistry;Catalytic behavior;	In a 10 mL round bottom flask containing 2 mL of (1 : 4) THF-H2O, Pd(OAc)2 (0.02 mmol), 3-(diphenylphosphino)benzoic acid (L 4 ), (0.04 mmol), CuI (0.05 mmol), 2-bromo benzaldehyde (1 mmol), phenylacetylene (1.2 mmol). K2CO3 (2 mmol), were added and the reaction mixture was stirred at 50 C for 2 h until the completion of the starting materials as monitored by TLC. Then NH4OAc (1.5 mmol) was added and again the whole reaction mixture was stirred at same temperature for additional 2 hours. After the formation of desired product 4a as confirmed by TLC, the reaction mixture was extracted with ethyl acetate (10 mL) and water (10 mL) and the organic layer was washed with aqueous saturated brine solution and dried over Na2SO4. The solvent was removed under vacuum, and the residue was purified by flash column chromatography on silica gel using ethyl acetate/ hexanes as the eluent to afford the desired product 4a.

References: [1]Journal of Organic Chemistry,2015,vol. 80,p. 11360 - 11368.
[2]Organic and Biomolecular Chemistry,2015,vol. 13,p. 3732 - 3741.
[3]Chinese Journal of Chemistry,2016,vol. 34,p. 857 - 860.
[4]Patent: CN109678798,2019,A .Location in patent: Paragraph 0014; 0015; 0016; 0017.
[5]Tetrahedron Letters,2020,vol. 61.
[6]Tetrahedron Letters,2019,vol. 60.
[7]European Journal of Organic Chemistry,2009,p. 2852 - 2862.
[8]Patent: CN105503722,2016,A .Location in patent: Paragraph 0032; 0033; 0034.
[9]Patent: CN107619389,2018,A .Location in patent: Paragraph 0014-0016.
[10]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 669 - 672.
[11]Journal of Organic Chemistry,2003,vol. 68,p. 920 - 928.
[12]Journal of Organic Chemistry,2003,vol. 68,p. 920 - 928.
[13]Journal of Organic Chemistry,2003,vol. 68,p. 920 - 928.
[14]Journal of Organic Chemistry,2003,vol. 68,p. 920 - 928.
[15]Journal of Organic Chemistry,2003,vol. 68,p. 920 - 928.
[16]Journal of Organic Chemistry,2003,vol. 68,p. 920 - 928.
[17]Journal of Organic Chemistry,2002,vol. 67,p. 3437 - 3444.
[18]Journal of Organic Chemistry,2002,vol. 67,p. 86 - 94.
[19]Organic letters,2001,vol. 3,p. 4035 - 4038.
[20]Organic letters,2001,vol. 3,p. 4035 - 4038.
[21]Organic letters,2001,vol. 3,p. 4035 - 4038.
[22]Organic letters,2001,vol. 3,p. 4035 - 4038.
[23]Journal of Organic Chemistry,1999,vol. 64,p. 6499 - 6504.
[24]Advanced Synthesis and Catalysis,2012,vol. 354,p. 1890 - 1896.
[25]Synthetic Communications,2013,vol. 43,p. 1714 - 1720.
[26]RSC Advances,2014,vol. 4,p. 38491 - 38497.
[27]RSC Advances,2014,vol. 40,p. 38491 - 38497.
[28]Chemical Communications,2015,vol. 51,p. 4097 - 4100.
[29]Synthesis,2016,vol. 48,p. 2057 - 2064.
[30]Synlett,2016,vol. 27,p. 2597 - 2600.
[31]Tetrahedron Letters,2019,vol. 60,p. 297 - 299.
[32]Inorganic Chemistry,2019,vol. 58,p. 10944 - 10954.
[33]Advanced Synthesis and Catalysis,2020,vol. 362,p. 1053 - 1057.
[34]Advanced Synthesis and Catalysis,2020,vol. 362,p. 1053 - 1057.
[35]Tetrahedron,2021,vol. 83.
[36]Advanced Synthesis and Catalysis,2021,vol. 363,p. 2664 - 2669.
[37]Organic Letters,2021,vol. 23,p. 3524 - 3529.

2
(E)-2-(2-phenylethynyl)benzaldehyde O-methyl-oxime [ No CAS ]
[ 37993-76-3 ]

References: [1]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 669 - 672.
[2]Advanced Synthesis and Catalysis,2009,vol. 351,p. 85 - 88.

3
(E)-tert-butyl([2-(2-phenylethynyl)phenyl]methylidene})amine [ No CAS ]
[ 37993-76-3 ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 86 - 94.
[2]Inorganic Chemistry,2019,vol. 58,p. 10944 - 10954.
[3]Organic Letters,1999,vol. 1,p. 553 - 556.
[4]Tetrahedron,2008,vol. 64,p. 11335 - 11348.
[5]Organic letters,2001,vol. 3,p. 2973 - 2976.
[6]Journal of Organic Chemistry,2003,vol. 68,p. 920 - 928.
[7]Organic letters,2001,vol. 3,p. 4035 - 4038.
[8]Organic Letters,2002,vol. 4,p. 193 - 196.

4
[ 696-62-8 ]
(E)-tert-butyl([2-(2-phenylethynyl)phenyl]methylidene})amine [ No CAS ]
[ 37993-76-3 ]
[ 320371-79-7 ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 920 - 928.
[2]Organic letters,2001,vol. 3,p. 4035 - 4038.

5
[ 58313-23-8 ]
(E)-tert-butyl([2-(2-phenylethynyl)phenyl]methylidene})amine [ No CAS ]
[ 37993-76-3 ]
4-(3-ethoxycarbonylphenyl)-3-phenylisoquinoline [ No CAS ]

References: [1]Organic letters,2001,vol. 3,p. 4035 - 4038.
[2]Organic letters,2001,vol. 3,p. 4035 - 4038.

6
[ 51934-41-9 ]
(E)-tert-butyl([2-(2-phenylethynyl)phenyl]methylidene})amine [ No CAS ]
[ 37993-76-3 ]
4-(4-ethoxycarbonylphenyl)-3-phenylisoquinoline [ No CAS ]

References: [1]Organic letters,2001,vol. 3,p. 4035 - 4038.
[2]Organic letters,2001,vol. 3,p. 4035 - 4038.

7
[ 2170-06-1 ]
(E)-N-(2-iodobenzylidene)-2-methylpropan-2-amine [ No CAS ]
[ 37993-76-3 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 8042 - 8051.
[2]Organic Letters,1999,vol. 1,p. 553 - 556.

8
[ 241813-23-0 ]
[ 37993-76-3 ]

References: [1]RSC Advances,2014,vol. 4,p. 38491 - 38497.
[2]RSC Advances,2014,vol. 40,p. 38491 - 38497.
[3]Chemistry - A European Journal,2012,vol. 18,p. 10602 - 10608,7.
[4]European Journal of Organic Chemistry,2015,vol. 2015,p. 5914 - 5918.
[5]Advanced Synthesis and Catalysis,2020,vol. 362,p. 1053 - 1057.

9
[ 591-50-4 ]
[ 201230-82-2 ]
(E)-tert-butyl([2-(2-phenylethynyl)phenyl]methylidene})amine [ No CAS ]
[ 52839-45-9 ]
[ 37993-76-3 ]
phenyl(3-phenylisoquinolin-4-yl)methanone [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 193 - 196.

10
[ 766-85-8 ]
[ 201230-82-2 ]
(E)-tert-butyl([2-(2-phenylethynyl)phenyl]methylidene})amine [ No CAS ]
[ 37993-76-3 ]
4-(3-methoxybenzoyl)-3-phenylisoquinoline [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 193 - 196.

11
[ 529-28-2 ]
[ 201230-82-2 ]
(E)-tert-butyl([2-(2-phenylethynyl)phenyl]methylidene})amine [ No CAS ]
[ 37993-76-3 ]
4-(2-methoxy-phenyl)-3-phenyl-isoquinoline [ No CAS ]
4-(2-methoxybenzoyl)-3-phenylisoquinoline [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 193 - 196.

12
[ 201230-82-2 ]
[ 696-62-8 ]
(E)-tert-butyl([2-(2-phenylethynyl)phenyl]methylidene})amine [ No CAS ]
[ 37993-76-3 ]
4-(4-methoxybenzoyl)-3-phenylisoquinoline [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 193 - 196.

13
[ 201230-82-2 ]
[ 455-13-0 ]
(E)-tert-butyl([2-(2-phenylethynyl)phenyl]methylidene})amine [ No CAS ]
[ 37993-76-3 ]
3-phenyl-4-(4-trifluoromethylbenzoyl)isoquinoline [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 193 - 196.

14
[ 201230-82-2 ]
[ 58313-23-8 ]
(E)-tert-butyl([2-(2-phenylethynyl)phenyl]methylidene})amine [ No CAS ]
[ 37993-76-3 ]
4-(3-ethoxycarbonylbenzoyl)-3-phenylisoquinoline [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 193 - 196.

15
[ 201230-82-2 ]
[ 98-88-4 ]
(E)-tert-butyl([2-(2-phenylethynyl)phenyl]methylidene})amine [ No CAS ]
[ 37993-76-3 ]
phenyl(3-phenylisoquinolin-4-yl)methanone [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 193 - 196.

16
[ 100-42-5 ]
(E)-tert-butyl([2-(2-phenylethynyl)phenyl]methylidene})amine [ No CAS ]
[ 37993-76-3 ]
3-phenyl-4-[(E)-2-phenylethen-1-yl]isoquinoline [ No CAS ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 3557 - 3560.

17
[ 111-34-2 ]
(E)-tert-butyl([2-(2-phenylethynyl)phenyl]methylidene})amine [ No CAS ]
[ 37993-76-3 ]
4-(1-n-butoxyethen-1-yl)-3-phenylisoquinoline [ No CAS ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 3557 - 3560.

18
[ 115-18-4 ]
(E)-tert-butyl([2-(2-phenylethynyl)phenyl]methylidene})amine [ No CAS ]
[ 37993-76-3 ]
(E)-2-methyl-4-(3-phenylisoquinolin-4-yl)-3-buten-2-ol [ No CAS ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 3557 - 3560.

19
[ 1663-39-4 ]
(E)-tert-butyl([2-(2-phenylethynyl)phenyl]methylidene})amine [ No CAS ]
[ 37993-76-3 ]
t-butyl (E)-3-(3-phenylisoquinolin-4-yl)acrylate [ No CAS ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 3557 - 3560.

20
[ 141-32-2 ]
(E)-tert-butyl([2-(2-phenylethynyl)phenyl]methylidene})amine [ No CAS ]
[ 37993-76-3 ]
n-butyl (E)-3-(3-phenylisoquinolin-4-yl)acrylate [ No CAS ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 3557 - 3560.
[2]Journal of Organic Chemistry,2003,vol. 68,p. 980 - 988.
[3]Journal of Organic Chemistry,2003,vol. 68,p. 980 - 988.

21
[ 5535-48-8 ]
(E)-tert-butyl([2-(2-phenylethynyl)phenyl]methylidene})amine [ No CAS ]
[ 37993-76-3 ]