521-73-3|Isoquinoline-1,3,4(2H)-trione| Ambeed

CAS No. :	521-73-3
Formula :	C₉H₅NO₃
M.W :	175.14
SMILES Code :	O=C1NC(C(C2=C1C=CC=C2)=O)=O
MDL No. :	MFCD01717158
InChI Key :	YIOFGHHAURBGSJ-UHFFFAOYSA-N
Pubchem ID :	10640

Safety of [ 521-73-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Application In Synthesis of [ 521-73-3 ]

* 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 [ 521-73-3 ]

[ 521-73-3 ] Synthesis Path-Downstream 1~54

1
[ 480-93-3 ]
[ 521-73-3 ]
4-(3-oxo-indolin-2-ylidene)-4H-isoquinoline-1,3-dione [ No CAS ]

References: [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1949,vol. 229,p. 372.

2
[ 481-98-1 ]
[ 521-73-3 ]

References: [1]Chemische Berichte,1900,vol. 33,p. 987.
Chemische Berichte,1901,vol. 34,p. 1654.

3
4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino)-4H-isoquinoline-1,3-dione [ No CAS ]
[ 521-73-3 ]

References: [1]Annales de Chimie (Cachan, France),1932,vol. <10>17,p. 271,383.

4
[ 95-57-8 ]
[ 521-73-3 ]
4,4-bis-(3-chloro-4-hydroxy-phenyl)-4H-isoquinoline-1,3-dione [ No CAS ]

References: [1]Patent: US2247899,1940,A .

5
[ 521-73-3 ]
[ 95-48-7 ]
4,4-bis-(4-hydroxy-3-methyl-phenyl)-4H-isoquinoline-1,3-dione [ No CAS ]

References: [1]Patent: US2247899,1940,A .

6
[ 521-73-3 ]
[ 618-40-6 ]
isoquinoline-1,3,4-trione-4-(methyl-phenyl-hydrazone) [ No CAS ]

References: [1]Annales de Chimie (Cachan, France),1932,vol. <10>17,p. 271,391.

7
[ 521-73-3 ]
[ 95-54-5 ]
[ 18605-37-3 ]

References: [1]Annales de Chimie (Cachan, France),1932,vol. <10>17,p. 271,401.

8
[ 521-73-3 ]
[ 100-63-0 ]
4-phenylazo-isoquinoline-1,3-diol [ No CAS ]

References: [1]Annales de Chimie (Cachan, France),1932,vol. <10> 17,p. 271,389.

9
[ 521-73-3 ]
[ 108-95-2 ]
4,4-bis-(4-hydroxy-phenyl)-4H-isoquinoline-1,3-dione [ No CAS ]

References: [1]Patent: US2247899,1940,A .

10
[ 521-73-3 ]
[ 56055-60-8 ]

References: [1]Annales de Chimie (Cachan, France),1932,vol. <10>17,p. 271,393,394.

11
[ 521-73-3 ]
7-amino-isoquinoline-1,3,4-trione [ No CAS ]

References: [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1957,vol. 244,p. 1651.

12
[ 110-00-9 ]
[ 521-73-3 ]
exo-1,3(2H,4H)-isoquinolinedione-4-spiro-6'-2'7'-dioxabicyclo<3,2,0>hept-3'-ene [ No CAS ]

References: [1]Tetrahedron,1994,vol. 50,p. 4987 - 4994.

13
[ 110-86-1 ]
[ 521-73-3 ]
[ 19171-27-8 ]

References: [1]Tetrahedron,1994,vol. 50,p. 4987 - 4994.

14
[ 26019-66-9 ]
[ 521-73-3 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 1463 - 1467.

15
[ 521-73-3 ]
[ 100-66-3 ]
1,3(2H,4H)-4-hydroxy-4-phenoxymethyl isoquinolinedione [ No CAS ]

References: [1]Tetrahedron,1994,vol. 50,p. 4987 - 4994.

16
[ 521-73-3 ]
[ 108-88-3 ]
1,3(2H,4H)-4-benzyl-4-hydroxy isoquinolinedione [ No CAS ]

References: [1]Tetrahedron,1994,vol. 50,p. 4987 - 4994.

17
[ 521-73-3 ]
[ 71-43-2 ]
[ 520-03-6 ]
[ 67213-84-7 ]

References: [1]Tetrahedron,1994,vol. 50,p. 4987 - 4994.
[2]Tetrahedron,1994,vol. 50,p. 4987 - 4994.

18
[ 1196-38-9 ]
[ 521-73-3 ]

References: [1]Chemical and Pharmaceutical Bulletin,1989,vol. 37,p. 3380 - 3381.

19
[ 4456-77-3 ]
[ 521-73-3 ]

References: [1]Chemical and Pharmaceutical Bulletin,1989,vol. 37,p. 3380 - 3381.
[2]Tetrahedron Letters,1998,vol. 39,p. 2381 - 2384.
[3]Tetrahedron,1999,vol. 55,p. 9185 - 9204.
[4]Tetrahedron Letters,1998,vol. 39,p. 2381 - 2384.
[5]Chemical Communications,2019,vol. 55,p. 8478 - 8481.

20
[ 513-81-5 ]
3-benzoyl-3-methoxy-2,3-dihydroisoquinoline-1,4-dione [ No CAS ]
[ 521-73-3 ]
[ 117362-75-1 ]
[ 65-85-0 ]

References: [1]Heterocycles,1988,vol. 27,p. 357 - 364.

21
[ 513-81-5 ]
3-acetoxy-3-benzoyl-2,3-dihydroisoquinoline-1,4-dione [ No CAS ]
[ 521-73-3 ]
[ 117362-75-1 ]
[ 65-85-0 ]

References: [1]Heterocycles,1988,vol. 27,p. 357 - 364.

22
[ 521-73-3 ]
[ 76283-09-5 ]
[ 159029-74-0 ]

References: [1]Heterocycles,1994,vol. 38,p. 1823 - 1838.

25
[ 521-73-3 ]
alkaline solution [ No CAS ]
[ 528-46-1 ]
(2-carbamoyl-phenyl)-glyoxylic acid [ No CAS ]

References: [1]Chemische Berichte,1900,vol. 33,p. 987.
Chemische Berichte,1901,vol. 34,p. 1654.

27
1.4-dioxy-isoquinoline [ No CAS ]
[ 521-73-3 ]

References: [1]Chemische Berichte,1902,vol. 35,p. 2422.

28
[ 521-73-3 ]
[ 501-65-5 ]
(E)-4-[benzoylphenylmethylene]-1,3-isoquinolinedione [ No CAS ]
(Z)-4-[benzoylphenylmethylene]-1,3-isoquinolinedione [ No CAS ]
7-benzoyl-5-aza-benzo[de]anthracene-4,6-dione [ No CAS ]

References: [1]Tetrahedron Letters,2000,vol. 41,p. 8141 - 8145.

29
[ 415963-42-7 ]
[ 521-73-3 ]
[ 76-05-1 ]
N-(4-chlorophenyl)-4-[3-(dimethylamino)propoxy]-N-{2-[2-(1,3-dioxo-2,3-dihydro-4(1H)-isoquinolinylidene)hydrazino]-2-oxoethyl}benzenesulfonamide trifluoroacetate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7882 - 7905.

30
[ 521-73-3 ]
[ 100-44-7 ]
[ 21640-35-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; at 0℃; for 3.5h;	3ml of concentrated sulfuric acid is placed in a 10ml beaker followed by adding 0.5ml of fuming nitric acid into slowly, the system is cooled in icewater bath. 500mg of compound III is added into the above solution when the temperature falls to less than 12C, it can be seen at once that the color of the reaction solution changes into deep red, the temperature also rises to more than 50C instantly. The raw material has disappeared by TLC analysis after 5 minutes, and the reaction is processed as follows: slowly adding 50ml of acetic ether to dilute the reaction solution, extracting with water, back-extracting the water phase with 30ml of acetic ether, washing the organic phases with water and saturated salt solution respectively, combining the organic phases, then drying, condensing, thereby obtaining product IV. 40mg of compound IV is dissolved in 1.5ml of anhydrous solvent (listed in the above), the system is cooled in icesalt bath. After the reaction is conducted for 30min upon adding 14mg of sodium hydride into the above solution, 0.20ml of benzyl chlorine is dropped into slowly. The reaction is processed as follows after progressed for 3 hours: extracting quickly with dichloromethane, drying, condensing, and the residue is applied on silica gel column (petroleum ether: acetic ether=8:1) to obtain compound V.

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1613 - 1623.
[2]Patent: EP1640367,2006,A1 .Location in patent: Page/Page column 12-13.

31
[ 521-73-3 ]
[ 103-63-9 ]
2-phenethyl-isoquinoline-1,3,4-trione [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1613 - 1623.

32
[ 521-73-3 ]
[ 824-94-2 ]
2-(4-methoxybenzyl)isoquinoline-1,3,4(2H)-trione [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1613 - 1623.

33
[ 521-73-3 ]
[ 107-05-1 ]
2-allylisoquinoline-1,3,4(2H)-trione [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1613 - 1623.

34
[ 521-73-3 ]
[ 352-11-4 ]
2-(4-fluorobenzyl)isoquinoline-1,3,4(2H)-trione [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1613 - 1623.

35
[ 521-73-3 ]
[ 74-88-4 ]
[ 21640-33-5 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1613 - 1623.

36
[ 703-59-3 ]
triethylorthoformate [ No CAS ]
[ 521-73-3 ]

References: [1]Tetrahedron,1999,vol. 55,p. 9185 - 9204.

37
[ 521-73-3 ]
2-<(4-bromo-2-fluorophenyl)methyl>spiro<1H-isoindole-1,5'-oxazolidine>-2',3(2H),4'-trione [ No CAS ]

References: [1]Heterocycles,1994,vol. 38,p. 1823 - 1838.

38
[ 521-73-3 ]
[ 159029-76-2 ]

References: [1]Heterocycles,1994,vol. 38,p. 1823 - 1838.

39
[ 521-73-3 ]
2-(4-Bromo-2-fluoro-benzyl)-1-carbamoyloxy-3-oxo-2,3-dihydro-1H-isoindole-1-carboxylic acid ethyl ester [ No CAS ]

References: [1]Heterocycles,1994,vol. 38,p. 1823 - 1838.

40
[ 85-44-9 ]
[ 521-73-3 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 1463 - 1467.
[2]Journal of the Chemical Society. Perkin transactions I,1990,p. 1463 - 1467.

41
[ 26019-65-8 ]
[ 521-73-3 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 1463 - 1467.

42
[ 129339-58-8 ]
[ 521-73-3 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 1463 - 1467.

43
3-acetyl-4-hydroxyisoquinolin-1(2H)-one [ No CAS ]
[ 521-73-3 ]

Yield	Reaction Conditions	Operation in experiment
	for 10h;Product distribution / selectivity;	2.0g of compound I is mixed with 3.76g of potassium carbonate thoroughly, then the resulting mixture is poured into a 25ml flask followed by adding 4.0ml of chloroacetone into, heating the solution to 90-110C (a reflux condensing tube is needed to be equipped on the flask, the system is protected with argon) while stirring, maintaining the temperature, and conducting the reaction for 3-4 hours. After the reaction is completed, excess chloroacetone is removed under a reduced pressure, into the residue is added a great deal of water, then filtrated with Buchner's filter. The resulting solid is washed twice with 10ml of 10% NaOH and 5-6 times with water respectively, dried under vacuum to obtain compound II; After a reflux condensing tube and a dropping funnel are connected on a three-necked bottle, 100ml of absolute methanol (or other anhydrous solvent) is added into the three-necked bottle, followed by slowly adding 0.23g of metallic sodium (or directly adding 10mmol of sodium methoxide). After the solid dissolves entirely, the solution is heated and refluxed, then compound II dissolved in absolute methanol (60ml CH3OH and 1.0g compound II) is dropped into by dropping funnel. After conducting the reflux for 2 hours the reaction is processed as follows: cooling the system with icewater bath, slowly neutralizing the reaction solution with 1M hydrochloride, continuing to stir for 30min in icewater bath after a large amount of solid emerge, filtrating to obtain a solid, then washing the solid with small amount of water, drying in vacuum, thereby obtaining compound III. 230mg of compound III is placed in a 25ml flask followed by adding 5ml solvent (listed in the above) into, air is blown into by a bubbler continuously. The reaction is completed after 10 hours and processed as follows: diluting the reaction solution with 30ml of acetic ether, extracting with water, back-extracting the water phase with 30ml of acetic ether, washing the organic phases with water and saturated salt solution respectively, combining the organic phases, then drying, condensing, the residue is applied on silica gel column (petroleum ether: acetic ether=2:1) to obtain compound IV
	With sulfuric acid; nitric acid; at 0 - 50℃; for 0.0833333h;Product distribution / selectivity;	3ml of concentrated sulfuric acid is placed in a 10ml beaker followed by adding 0.5ml of fuming nitric acid into slowly, the system is cooled in icewater bath. 500mg of compound III is added into the above solution when the temperature falls to less than 12C, it can be seen at once that the color of the reaction solution changes into deep red, the temperature also rises to more than 50C instantly. The raw material has disappeared by TLC analysis after 5 minutes, and the reaction is processed as follows: slowly adding 50ml of acetic ether to dilute the reaction solution, extracting with water, back-extracting the water phase with 30ml of acetic ether, washing the organic phases with water and saturated salt solution respectively, combining the organic phases, then drying, condensing, thereby obtaining product IV. 40mg of compound IV is dissolved in 1.5ml of anhydrous solvent (listed in the above), the system is cooled in icesalt bath. After the reaction is conducted for 30min upon adding 14mg of sodium hydride into the above solution, 0.20ml of benzyl chlorine is dropped into slowly. The reaction is processed as follows after progressed for 3 hours: extracting quickly with dichloromethane, drying, condensing, and the residue is applied on silica gel column (petroleum ether: acetic ether=8:1) to obtain compound V.

References: [1]Patent: EP1640367,2006,A1 .Location in patent: Page/Page column 12-13.
[2]Patent: EP1640367,2006,A1 .Location in patent: Page/Page column 12-13.

44
[ 938-24-9 ]
[ 521-73-3 ]