18528-78-4|2,3-Dihydro-1H-cyclopenta[b]quinolin-9-amine| Ambeed

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Quality Control of [ 18528-78-4 ] Purity: 98% SDS Specification

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Product Details of [ 18528-78-4 ]

CAS No. :	18528-78-4
Formula :	C₁₂H₁₂N₂
M.W :	184.24
SMILES Code :	NC1=C(CCC2)C2=NC3=CC=CC=C13
MDL No. :	MFCD00618440
InChI Key :	GYSCQDBTSDBCGY-UHFFFAOYSA-N
Pubchem ID :	205772

Safety of [ 18528-78-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Application In Synthesis of [ 18528-78-4 ]

* 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 [ 18528-78-4 ]

[ 18528-78-4 ] Synthesis Path-Downstream 1~22

1
[ 40528-00-5 ]
[ 18528-78-4 ]

References: [1]Journal of the Chemical Society,1947,p. 634,637.

2
[ 18528-78-4 ]
[ 108-24-7 ]
N-(2,3-dihydro-1H-cyclopenta[b]quinolin-9-yl)-acetamide [ No CAS ]

References: [1]Journal of the Chemical Society,1947,p. 634,637.

3
[ 18528-78-4 ]
[ 108-24-7 ]
N-(2,3-dihydro-1H-cyclopenta[b]quinolin-9-yl)-diacetamide [ No CAS ]

References: [1]Journal of the Chemical Society,1947,p. 634,637.

4
[ 18528-78-4 ]
[ 117863-94-2 ]

References: [1]Annales de Chimie (Cachan, France),1959,vol. <13> 4,p. 87,108.

5
[ 97183-64-7 ]
[ 18528-78-4 ]

References: [1]Annales de Chimie (Cachan, France),1959,vol. <13> 4,p. 87,108.

6
[ 120-92-3 ]
[ 1885-29-6 ]
[ 18528-78-4 ]

Yield	Reaction Conditions	Operation in experiment
	With boron trifluoride; In toluene; for 24.0h;Reflux;	General procedure: To a solution of 2-aminobenzonitrile (1.0 mmol) and cyclic ketones (2a-c, n=1, 2 and 3; 1.0 mmol) in dry toluene(8 mL), boron triflurodietherate (1.28 mL) was added slowly with a syringe. The mixture was refluxed for 24 hours with stirring. After cooling the mixture to room temperature, the mixture was dried and the residue thus obtained was treated with 2M NaOH (24 mL) and refluxedfurther for 24 hours. After cooling, the mixture was extracted with CHCl3. The combined organic extracts were evaporated to give colorless to yellow solids (3a-c).

References: [1]Green Chemistry,2011,vol. 13,p. 958 - 964.
[2]Pharmaceutical Chemistry Journal,1993,vol. 26,p. 769 - 772.
[3]Journal of Medicinal Chemistry,1997,vol. 40,p. 3516 - 3523.
[4]Combinatorial Chemistry and High Throughput Screening,2022,vol. 25,p. 167 - 186.

8
[ 120-92-3 ]
[ 1885-29-6 ]
[ 18528-78-4 ]
[ 1135-80-4 ]

References: [1]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 533 - 542.

9
[ 18528-77-3 ]
[ 18528-78-4 ]

References: [1]Organic Letters,2013,vol. 15,p. 4794 - 4797.

10
[ 18528-78-4 ]
[ 2162-98-3 ]
N,N′-(decane-1,10-diyl)bis(9-amino-2,3-dihydro-1H-cyclopenta[b]quinolinium)dichloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4.5%	In sulfolane; at 190 - 200℃; for 90.0h;	A mixture of <strong>[18528-78-4]2,3-dihydro-1H-cyclopenta[b]quinolin-9-ylamine</strong> (0.45 g, 2.44 mmol), 1,10-dichlorodecane (0.25 g, 1.2mmol), and sulfolane (2 mL) was heated at 190-200 C for 90 h. The resulting mass was stirred with methanol and filtered. The filtrate was concentrated and chromatographedon an Al2O3 column using a gradient from 1 to 25% ofmethanol in methylene chloride. Fractions containing required product were pooled together and evaporated, andthe resulting off-white solid (31 mg, 4.5%) was further purified by crystallization from a methanol/acetone mixture [Mp 250-258 C (dec). 1H NMR (500 MHz, CDCl3) δ1.27-1.43 (m, 12 H), 1.67-1.76 (m, 4 H), 2.20-2.26 (m, 4H), 2.95 (t, 4 H, J = 7.5 Hz), 3.38 (t, 4 H, J = 7.5 Hz), 3.63(t, 4 H, J = 7.0 Hz), 4.46 (t, 4 H, J = 6.5 Hz),7.72 (t, 2 H, J = 7.0 Hz), 7.98 (t, 2 H, J = 7.5 Hz),8.15 (d, 2 H, J = 9.0 Hz), 8.54 (d with fine splitting, 2 H,J = 8.5 Hz), 8.92 (br s, 4 H, NH2).
	In sulfolane; at 190 - 200℃; for 10.0h;	General procedure: General methods for the synthesis of CABs are reported in Sharma et al. 2018 (Supra) and summarized in FIG. 5. Methods described in FIG. 5 are a) Amyl alcohol, reflux under N2, 12 h; b) No solvent, 180-195 C, 2 h; c) sulfolane, 190-200 C, 10 h. Three new CABs e.g. APDE-8, CODE-9 and CYDE-21 were successfully synthesized using the methods shown in FIG. 5.

References: [1]Journal of Antibiotics,2018,vol. 71,p. 713 - 721.
[2]Patent: WO2022/98934,2022,A1 .Location in patent: Page/Page column 30; 31.

11
[ 18528-78-4 ]
[ 4635-59-0 ]
C₁₆H₁₇ClN₂O [ No CAS ]