4,5-Dimethoxyisatoic anhydride | Other Aromatic Heterocycles

4,5-Dimethoxyisatoic anhydride is a compound with antioxidant and anti-inflammatory properties, mainly used as a synthetic intermediate in the preparation of other bioactive compounds.

4.5 *For Research Use Only !

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Quality Control of 4,5-Dimethoxyisatoic anhydride Purity: 97% SDS Specification

COA

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NMR

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CNMR

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Product Details of 4,5-Dimethoxyisatoic anhydride

CAS No. :	20197-92-6
Formula :	C₁₀H₉NO₅
M.W :	223.18
SMILES Code :	O=C(NC1=CC(OC)=C(OC)C=C12)OC2=O
MDL No. :	MFCD03426390
InChI Key :	SHWCMBUPQTWNES-UHFFFAOYSA-N
Pubchem ID :	2758423

Safety of 4,5-Dimethoxyisatoic anhydride

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H317-H319-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of 4,5-Dimethoxyisatoic anhydride

* 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 [ 20197-92-6 ]

[ 20197-92-6 ] Synthesis Path-Downstream 1~35

1
[ 75-44-5 ]
[ 5653-40-7 ]
[ 20197-92-6 ]

References: [1]Journal of medicinal chemistry,1968,vol. 11,p. 130 - 136.
[2]European Journal of Medicinal Chemistry,1983,vol. 18,p. 241 - 247.

2
[ 75-44-5 ]
[ 26759-46-6 ]
[ 20197-92-6 ]

References: [1]Synthesis,1981,p. 391 - 392.

3
[ 20197-92-6 ]
[ 42897-48-3 ]
[ 127931-56-0 ]

References: [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 1535 - 1539.

4
[ 20197-92-6 ]
[ 4338-95-8 ]
[ 16175-67-0 ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 703 - 708.

5
[ 20197-92-6 ]
[ 41306-45-0 ]
[ 17148-62-8 ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 703 - 708.

6
[ 20197-92-6 ]
[ 6972-04-9 ]
[ 16175-61-4 ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 703 - 708.

7
[ 20197-92-6 ]
[ 75191-77-4 ]
[ 17148-68-4 ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 703 - 708.

8
[ 20197-92-6 ]
[ 37429-98-4 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 735 - 742.

9
[ 21560-74-7 ]
[ 20197-92-6 ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 703 - 708.
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2299 - 2302.

10
[ 20197-92-6 ]
[ 57-14-7 ]
[ 87296-91-1 ]

References: [1]European Journal of Medicinal Chemistry,1983,vol. 18,p. 241 - 247.

11
[ 20197-92-6 ]
[ 106-95-6 ]
[ 64675-74-7 ]

References: [1]Synthesis,1981,p. 391 - 392.

12
[ 20197-92-6 ]
[ 407-25-0 ]
[ 95274-63-8 ]

References: [1]Journal of Organic Chemistry,1985,vol. 50,p. 1246 - 1255.

13
[ 20197-92-6 ]
[ 74-88-4 ]
[ 57384-36-8 ]

Yield	Reaction Conditions	Operation in experiment
89%		9.0Og (40.3 mmol) 6,7-Dimethoxy-lH-benzo(d)(l,3)oxazine-2,4-dione were dissolved in 60 ml dried dimethylformamide and cooled to 0 0C. 1.32g (52.3mmol) sodium hydride was added and the solution was stirred for 30 min at room temperature (Argon). After cooling to 0 0C again 7.42 g (3.27 ml, 52.3 mmol) iodomethane was added and stirred at room temperature for 1 h. 300 ml water was added and the residue is filtrated, rinsed with water and ethyl ether. Yield: 8.5 g=89percent Grey powder
59%		To a solution of 500 mg (3.06 mmol) of <strong>[20197-92-6]6,7-dimethoxy-1,2-dihydro-4H-3,1-benzoxazine-2,4-dione</strong> (XV), in 6 ml of anhydrous DMF, add under an inert atmosphere 134 mg (3.37 mmol) of 60percent NaH in oil.After 10 minutes at room temperature, add dropwise 219 mul (3.52 mmol) of MeI. Allow to stand at room temperature for 3 hours. Add 40 ml of a water-ice mixture.Filter the precipitate and wash twice with 1 ml of EtOH and 3 ml of Et2O. One obtains 320 mg of the abovenamed product in the form of a white powder. Yield: 59percent. 1H-NMR (CDCl3, 300 MHz): d 3.31 (s, 3H, 1-CH3), 3.82 (s, 3H, OCH3), 3.96 (s, 3H, OCH3), 6.85 (s, 1H Ar), 7.32 (s, 1H Ar).
59%		6,7-dimethoxy-1-methyl-1,2-dihydro-4H-3,1-benzoxazine-2,4-dione, 14a; Under an inert atmosphere, 134 mg (3.37 mmoles) of 60percent NaH in oil were added to a solution of 500 mg (3.06 mmoles) of <strong>[20197-92-6]6,7-dimethoxy-1,2-dihydro-4H-3,1-benzoxazine-2,4-dione</strong> 13a in 6 ml of anhydrous DMF. After 10 min at room temperature, 219 mul (3.52 mmoles) of Mel were added dropwise. The reaction was left at room temperature for 3 h, then 40 ml of a water-ice mixture were added. The precipitate was filtered and washed with 2.x.1 ml of EtOH and 3 ml of Et2O. The reaction produced 320 mg of the above product in the form of a white powder. Yield: 59percent. 1H NMR (CDCl3, 300 MHz): d 3.31 (s, 3H, -CH3), 3.82 (s, 3H, OCH3), 3.96 (s, 3H, OCH3), 6.85 (s, 1H Ar), 7.32 (s, 1H Ar).

References: [1]Patent: WO2008/52742,2008,A1 .Location in patent: Page/Page column 20; Sheet 3; Sheet 7.
[2]Patent: US2004/152888,2004,A1 .Location in patent: Page/Page column 17.
[3]Patent: US2006/128695,2006,A1 .Location in patent: Page/Page column 20.
[4]Organic Letters,2011,vol. 13,p. 486 - 489.
[5]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 1217 - 1221.

14
[ 20197-92-6 ]
[ 23356-96-9 ]
(2-Amino-4,5-dimethoxy-phenyl)-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-methanone [ No CAS ]

References: [1]Synlett,1997,vol. 1997,p. 75 - 78.

15
[ 20197-92-6 ]
methyl halide [ No CAS ]
[ 57384-36-8 ]

References: [1]Journal of Heterocyclic Chemistry,1975,vol. 12,p. 565 - 572.

16
[ 20197-92-6 ]
p-fluorobenzyl halide [ No CAS ]
[ 57384-87-9 ]

References: [1]Journal of Heterocyclic Chemistry,1975,vol. 12,p. 565 - 572.

18
[ 20197-92-6 ]
PS-Wang resin-cyanoacetate [ No CAS ]
3-cyano-6,7-dimethoxy-4-hydroxyquinolin-2(1H)-one [ No CAS ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 6399 - 6402.

19
[ 20197-92-6 ]
[ 91-56-5 ]
2,3-dimethoxyindolo[2,1-b]quinazolin-6,12-dione [ No CAS ]

References: [1]Synthesis,2009,p. 3642 - 3648.
[2]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 2303 - 2307.
[3]Acta Pharmacologica Sinica,2010,vol. 31,p. 259 - 264.
[4]Heterocyclic Communications,2015,vol. 21,p. 67 - 71.

20
[ 367-21-5 ]
[ 20197-92-6 ]
2-amino-N-(3-chloro-4-fluorophenyl)-4,5-dimethoxybenzamide [ No CAS ]