[ CAS No. 38609-97-1 ] {[proInfo.proName]}

Name: 38609-97-1|2-(9-Oxoacridin-10(9H)-yl)acetic acid|98%
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SKU: A266566
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Quality Control of [ 38609-97-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 38609-97-1 ]

Product Details of [ 38609-97-1 ]

CAS No. :	38609-97-1	MDL No. :	MFCD00157050
Formula :	C₁₅H₁₁NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UOMKBIIXHQIERR-UHFFFAOYSA-N
M.W :	253.25	Pubchem ID :	38072
Synonyms :

Safety of [ 38609-97-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 38609-97-1 ]

* 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 [ 38609-97-1 ]
Downstream synthetic route of [ 38609-97-1 ]

[ 38609-97-1 ] Synthesis Path-Upstream 1~14

1
[ 79-11-8 ]
[ 578-95-0 ]
[ 38609-97-1 ]

Yield	Reaction Conditions	Operation in experiment
95.7%	at 20 - 25℃; for 12 h; Ionic liquid	The synthesis method comprises the following steps:29.2 g of [Pmim] OH ionic liquid was added in a three-necked flask equipped with a condensing reflux at room temperature,19.5g acridone, stirring evenly after adding 11.3 g of chloroacetic acid, the control temperature of 25 stirring reaction 12h after standing at room temperatureThe residue was then washed with 25 ml of methanol and dried to give 24.2 g of acridone acetate (yield: 95.7percent).
93.5%	With tetrabutylammomium bromide; sodium hydroxide In water; N,N-dimethyl-formamide at 80℃; for 3 h;	39percent acridone (2 mol),N-tetrabutylammonium bromide (TBAB) 19.34g (0.06mol),265 g (2.8 mol) of chloroacetic acid was added to a 1000 mL three-necked flask.Add 500 mL of organic solvent DMF and stir at 80 ° C to dissolve.Further, 100 mL of a 60 wtpercent NaOH aqueous solution was added, and after heating at 80 ° C for 3 hours,The reaction was stopped, allowed to cool to room temperature, and the reaction system was poured into 300 mL of ice water.A large amount of yellow solid precipitates were precipitated, allowed to stand overnight, suction filtered, and washed with ice water.That is, a wet intermediate is obtained; 500 mL of a 30 wtpercent NaOH aqueous solution is added to the wet intermediate,Dissolve and stir at room temperature, filter, and wash with 100 mL of 30 wtpercent NaOH aqueous solution.Combine the washing solution, add concentrated hydrochloric acid to adjust the pH value between 4 and 5.There is a large amount of yellow solid precipitates, Allow to stand overnight, suction filtration, wash with ice water,Drying, 474 g of acridinone acetate product was obtained, and the yield was 93.5percent.The purity by HPLC was 99.2percent.

Reference： [1] Patent: CN104592115, 2017, B, . Location in patent: Paragraph 0016; 0017; 0018
[2] Patent: CN108456166, 2018, A, . Location in patent: Paragraph 0030; 0044; 0045; 0047; 0050; 0051; 0072
[3] Acta Poloniae Pharmaceutica - Drug Research, 2010, vol. 67, # 2, p. 211 - 214

2
[ 105-36-2 ]
[ 578-95-0 ]
[ 38609-97-1 ]

Reference： [1] Organic Letters, 2017, vol. 19, # 1, p. 94 - 97
[2] Organic Preparations and Procedures International, 2000, vol. 32, # 3, p. 284 - 287

3
[ 77778-90-6 ]
[ 38609-97-1 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 12, p. 3593 - 3615

4
[ 38609-90-4 ]
[ 38609-97-1 ]

Reference： [1] European Journal of Medicinal Chemistry, 2007, vol. 42, # 6, p. 752 - 771

5
[ 122-39-4 ]
[ 38609-97-1 ]

Reference： [1] Organic Letters, 2017, vol. 19, # 1, p. 94 - 97

6
[ 606-87-1 ]
[ 38609-97-1 ]

Reference： [1] Organic Letters, 2017, vol. 19, # 1, p. 94 - 97

7
[ 552-82-9 ]
[ 38609-97-1 ]

Reference： [1] Organic Letters, 2017, vol. 19, # 1, p. 94 - 97

8
[ 77778-87-1 ]
[ 38609-97-1 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 12, p. 3593 - 3615
[2] Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 12, p. 3593 - 3615

9
[ 578-95-0 ]
[ 38609-97-1 ]

Reference： [1] European Journal of Medicinal Chemistry, 2007, vol. 42, # 6, p. 752 - 771

10
[ 77778-88-2 ]
[ 38609-97-1 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 12, p. 3593 - 3615

11
[ 85793-68-6 ]
[ 38609-97-1 ]

Reference： [1] Chemische Berichte, 1923, vol. 56, p. 1829

12
[ 91-40-7 ]
[ 38609-97-1 ]

Reference： [1] Acta Poloniae Pharmaceutica - Drug Research, 2010, vol. 67, # 2, p. 211 - 214

13
[ 62-53-3 ]
[ 38609-97-1 ]

Reference： [1] Acta Poloniae Pharmaceutica - Drug Research, 2010, vol. 67, # 2, p. 211 - 214

14
[ 118-91-2 ]
[ 38609-97-1 ]

Reference： [1] Acta Poloniae Pharmaceutica - Drug Research, 2010, vol. 67, # 2, p. 211 - 214

[ 38609-97-1 ] Synthesis Path-Downstream 1~58

1
[ 85793-68-6 ]
[ 38609-97-1 ]

Reference： [1]Chemische Berichte,1923,vol. 56,p. 1829

2
[ 67-56-1 ]
[ 38609-97-1 ]
[ 59922-61-1 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1980,vol. 45,p. 3593 - 3615

3
[ 38609-97-1 ]
[ 623-33-6 ]
[ 124985-01-9 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1988,vol. 330,p. 1023 - 1029

4
[ 38609-97-1 ]
[ 2743-40-0 ]
[ 124985-02-0 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1988,vol. 330,p. 1023 - 1029

5
[ 38609-97-1 ]
[ 58880-43-6 ]

Reference： [1]Pharmazie,1986,vol. 41,p. 326 - 328

6
[ 77778-90-6 ]
[ 38609-97-1 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1980,vol. 45,p. 3593 - 3615

Yield	Reaction Conditions	Operation in experiment
	Erhitzen;

11
[ 105-36-2 ]
[ 578-95-0 ]
[ 38609-97-1 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 94 - 97
[2]Organic Preparations and Procedures International,2000,vol. 32,p. 284 - 287

12
[ 38609-97-1 ]
[ 78486-14-3 ]
C₁₃H₈NOCH₂CONHC₄H₂NCH₃CONH(CH₂)3N(CH₃)2 [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 752 - 771

13
[ 38609-97-1 ]
[ 78486-16-5 ]
C₁₃H₈NOCH₂CO(NHC₄H₂NCH₃CO)2NH(CH₂)3N(CH₃)2 [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 752 - 771

14
[ 38609-90-4 ]
[ 38609-97-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In ethanol; water; at 60℃; for 1h;	General procedure: Intermediate ethyl 2-(9-oxoacridin-10(9H)-yl) acetate was synthesizedby the method of 13b. To the solution of ethyl 2-(9-oxoacridin-10(9H)-yl) acetate (0.30g, 1.1 mmol) and NaOH (0.05g, 1.3 mmol) inethanol (20 ml) and water (2 ml) was added, and the mixture washeated to 60 for 1 h. Upon removal of the solvents, the resulting residuewas dissolved in water and filtered. After neutralization of thefiltrate with conc.HCl, the mixture was filtrated to get the crude solid,subsequently recrystallized by methanol for 0.2g white power, theyield: 73.3%. 1H NMR (400 MHz, DMSO-D6) delta (ppm): 13.40 (s, 1H),8.37 (d, J = 1.6 Hz, 1H), 8.35 (d, J = 1.6 Hz, 1H), 7.82 (ddd, J = 8.7,6.9, 1.7 Hz, 2H), 7.69 (s, 1H), 7.67 (s, 1H), 7.36 (t, J = 7.4 Hz, 2H),5.34 (s, 2H). 13C NMR (101 MHz, DMSO-D6) delta (ppm): 177.20, 170.58,142.65 (2C), 134.77 (2C), 127.16 (2C), 122.12 (2C), 122.06(2C),116.31 (2C), 48.02. HRMS (ESI) m/z [M+H] + calculated forC15H11NO3: 254.0817 found: 254.0811.

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 752 - 771
[2]Bioorganic Chemistry,2020,vol. 95

15
[ 578-95-0 ]
[ 38609-97-1 ]

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 752 - 771
[2]Bioorganic Chemistry,2020,vol. 95

16
[ 77778-87-1 ]
[ 38609-97-1 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1980,vol. 45,p. 3593 - 3615
[2]Collection of Czechoslovak Chemical Communications,1980,vol. 45,p. 3593 - 3615

17
[ 77778-88-2 ]
[ 38609-97-1 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1980,vol. 45,p. 3593 - 3615

18
[ 288-32-4 ]
nickel(II) chloride hexahydrate [ No CAS ]
[ 38609-97-1 ]
[ 919109-45-8 ]

Reference： [1]Inorganic Chemistry,2006,vol. 45,p. 10479 - 10486

19
[ 14216-22-9 ]
[ 38609-97-1 ]
[ 937021-67-5 ]

Yield	Reaction Conditions	Operation in experiment
	In water; for 0.416667 - 0.583333h;Heating / reflux;	A. Under intensive stirring, 25,3 g of 9-oxoacridine-10-acetic acid, 40 ml of distilled water and 0,1 mole (20,1 g) of 1-deoxy-1-N-(ethylamino)-D-glucitol are placed to a retort with backflow condenser. The mixture is boiled for 25-35 min., then it is cooled to room temperature and 100 ml of acetone is added with intensive stirring. The laid down sediment is filtered, washed by 50 ml of absolute ethanol and is dried under reduced pressure for 1 hour to provide in accordance with the selected 1-alkylamino-1-deoxypolyol: N-(1-deoxy-D-glucitol-1-yl)-N-ethyl ammonium 9-oxoacridine-10-ylacetate (1) Found: N H C Brutto formula 6,08 6,57 59,95C23H30N2O8 Calculated: N H C Mm =462,49 6,06 6,54 59,73 NMR spectra (D2O): 1.28 (3H, t, CH3), 2.84-3.16 (4H, m, CH2), 3.77-3.89 (6H, m, CH2, CH), 4.10 (2H, s, CH2), 7.23 - 7.58 (4H, m, Ar), 7.79 - 7.96 (2H, m, Ar), 8.22 - 8.39 (2H, m, Ar). Melting point: 130-133 C.

Reference： [1]Patent: EP1970372,2008,A2 .Location in patent: Page/Page column 16

20
[ 937021-85-7 ]
[ 38609-97-1 ]
[ 937021-86-8 ]

Yield	Reaction Conditions	Operation in experiment
	In water;	B. 103,3 g of 1-deoxy-1-N-(propylamino)-L-galactitol is dissolved In 200 ml of water and then 125,3 g of well-milled powder of 9-oxoacridine-10-acetic acid is added in the solution, in small portions, under stirring until complete dissolution. 1000 ml of absolute ethanol is added. The laid down sediment is filtered washed on the filter by 150 ml of absolute ethanol and is dried under reduced pressure at 60 C for 1 hour to provide in accordance with the selected 1-alkylamino-1-deoxypolyol: N-(1-deoxy-D- galactitol -1-yl)-N-propyl ammonium 9-oxoacridine-10-ylacetate (2) Found: N H C Brutto formula 5,75 6,73 60,58C24H32N2O8 Calculated: N H C Mm =476,51 5,78 6,77 60,49 NMR spectra (D2O): 1.28 (3H, t, CH3), 1.84 (1H, m, CH2), 2.38 (1H, q, CH2), 2.84 - 3.16 (4H, m, CH2), 3.77 - 3.89 (6H, m, CH2, CH), 4.10 (2H, c, CH2), 7.23 - 7.58 (4H, m, Ar), 7.79 - 7.96 (2H, m, Ar), 8.22 - 8.39 (2H, m, Ar). Melting point: 127-130 C.

Reference： [1]Patent: EP1970372,2008,A2 .Location in patent: Page/Page column 16

21
[ 146339-93-7 ]
[ 38609-97-1 ]
[ 937021-76-6 ]

Yield	Reaction Conditions	Operation in experiment
	In water; for 0.333333h;Heating / reflux;	C) 100 g of 9-oxoacridine-10-acetic acid and 150 ml of distilled water are placed to a retort with backflow condenser and then 93,6 g of 1-deoxy-1-N-(butylamino)-D-mannitol is added under intensive stirring. The obtained mixture is boiled for 20 min until complete dissolution. The solution is cooled to 20-22 C and mixed with 100 ml of acetone. The retort with laid down sediment is cooled in melting ice (0-1 C) for 4 hours. Then the sediment is filtered and washed on filter by 40 ml of cooled acetone and dried under reduced pressure at 60 C to provide in accordance with the selected 1-alkylamino-1-deoxypolyol: N-(1-deoxy-D-mannitol-1-yl)- N-butyl ammonium 9-oxoacridine-10-ylacetate (3) Found: N H C Brutto formula 5,74 6,95 61,15C25H34N2O8 Calculated: N H C Mm =490,55 5,71 6,99 61,21 NMR spectra (D2O): 1.28 (3H, t, CH3), 1.62-1.70 (1H, m, CH2), 1.80 -1.95 (2H, m, CH2), 2.30 (1H, q, CH2), 2.84 - 3.16 (4H, m, CH2), 3.77 - 3.89 (6H, m, CH2, CH), 4.10. (2H, s, CH2), 7.23 - 7.58 (4H, m, Ar), 7.79 - 7.96 (2H, m, Ar), 8.22 - 8.39 (2H, m, Ar). Melting point: 126-129 C.

Reference： [1]Patent: EP1970372,2008,A2 .Location in patent: Page/Page column 16-17

22
[ 91-40-7 ]
[ 38609-97-1 ]

Reference： [1]Acta poloniae pharmaceutica,2010,vol. 67,p. 211 - 214
[2]Bioorganic Chemistry,2020,vol. 95

23
[ 79-11-8 ]
[ 578-95-0 ]
[ 38609-97-1 ]

Yield	Reaction Conditions	Operation in experiment
95.7%	With [Pmim]OH; at 20 - 25℃; for 12h;Ionic liquid;	The synthesis method comprises the following steps:29.2 g of [Pmim] OH ionic liquid was added in a three-necked flask equipped with a condensing reflux at room temperature,19.5g acridone, stirring evenly after adding 11.3 g of chloroacetic acid, the control temperature of 25 stirring reaction 12h after standing at room temperatureThe residue was then washed with 25 ml of methanol and dried to give 24.2 g of acridone acetate (yield: 95.7%).
93.5%	With tetrabutylammomium bromide; sodium hydroxide; In water; N,N-dimethyl-formamide; at 80℃; for 3h;	39% acridone (2 mol),N-tetrabutylammonium bromide (TBAB) 19.34g (0.06mol),265 g (2.8 mol) of chloroacetic acid was added to a 1000 mL three-necked flask.Add 500 mL of organic solvent DMF and stir at 80 C to dissolve.Further, 100 mL of a 60 wt% NaOH aqueous solution was added, and after heating at 80 C for 3 hours,The reaction was stopped, allowed to cool to room temperature, and the reaction system was poured into 300 mL of ice water.A large amount of yellow solid precipitates were precipitated, allowed to stand overnight, suction filtered, and washed with ice water.That is, a wet intermediate is obtained; 500 mL of a 30 wt% NaOH aqueous solution is added to the wet intermediate,Dissolve and stir at room temperature, filter, and wash with 100 mL of 30 wt% NaOH aqueous solution.Combine the washing solution, add concentrated hydrochloric acid to adjust the pH value between 4 and 5.There is a large amount of yellow solid precipitates, Allow to stand overnight, suction filtration, wash with ice water,Drying, 474 g of acridinone acetate product was obtained, and the yield was 93.5%.The purity by HPLC was 99.2%.

Reference： [1]Patent: CN104592115,2017,B .Location in patent: Paragraph 0016; 0017; 0018
[2]Patent: CN108456166,2018,A .Location in patent: Paragraph 0030; 0044; 0045; 0047; 0050; 0051; 0072
[3]Acta poloniae pharmaceutica,2010,vol. 67,p. 211 - 214

24
[ 62-53-3 ]
[ 38609-97-1 ]

Reference： [1]Acta poloniae pharmaceutica,2010,vol. 67,p. 211 - 214
[2]Bioorganic Chemistry,2020,vol. 95

25
[ 118-91-2 ]
[ 38609-97-1 ]

Reference： [1]Acta poloniae pharmaceutica,2010,vol. 67,p. 211 - 214

26
[ 38609-97-1 ]
C₁₅H₁₀NO₆S^(1-) [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2013,vol. 83,p. 691 - 693
Zh. Obshch. Khim.,2013,vol. 83,p. 604 - 607,4

27
[ 38609-97-1 ]
[ 719-54-0 ]
C₁₅H₁₀NO₆S^(1-) [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2013,vol. 83,p. 691 - 693
Zh. Obshch. Khim.,2013,vol. 83,p. 604 - 607,4

28
[ 122-39-4 ]
[ 38609-97-1 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 94 - 97

29
[ 606-87-1 ]
[ 38609-97-1 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 94 - 97

30
[ 552-82-9 ]
[ 38609-97-1 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 94 - 97

31
[ 38609-97-1 ]
C₁₉H₁₉N₃O₂ [ No CAS ]