32566-01-1|2-(1H-Indol-2-yl)aniline| Ambeed

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Quality Control of [ 32566-01-1 ] Purity: 97% SDS Specification

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Product Details of [ 32566-01-1 ]

CAS No. :	32566-01-1
Formula :	C₁₄H₁₂N₂
M.W :	208.26
SMILES Code :	NC1=CC=CC=C1C(N2)=CC3=C2C=CC=C3
MDL No. :	MFCD00134432
InChI Key :	IAKRGXQCKYFJCB-UHFFFAOYSA-N
Pubchem ID :	735966

Safety of [ 32566-01-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319
Precautionary Statements:	P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 32566-01-1 ]

* 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.

Downstream synthetic route of [ 32566-01-1 ]

[ 32566-01-1 ] Synthesis Path-Downstream 1~36

1
[ 32566-01-1 ]
[ 108-24-7 ]
[ 58995-86-1 ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 2561 - 2568.
[2]Journal of the Chemical Society,1956,p. 1319,1329.

2
[ 32566-01-1 ]
[ 98-88-4 ]
[ 58995-87-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine; at 0℃;	Compound 135-1 (94 g, 0.451 mol) and triethylamine (42 mL, 0.451 mol) are dissolved in 1200 mL of MC. Benzoyl chloride (69.7 g, 0.496 mol) is dissolved in 300 mL of MC and then slowly added dropwise to the mixture at 0 C. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO 4, the solvent was removed by a rotary evaporator to obtain a liquid form compound 135-2 (112 g, 80%).
72%	With pyridine;	EXAMPLE 18 2-(2'-N-Benzoylamino-phenyl)-indole 2.4 ml of benzoyl chloride were added in one operation to a solution of 8 ml of dry pyridine containing 4.16 g (0.02 mol) of 2-(2'-aminophenyl)-indole, prepared as in Example 5. The precipitate was centrifuged out, washed several times with cold water and recrystallized from aqueous ethanol to give 4.5 g of 2-(2'-N-benzoylamino-phenyl)-indole. M.P.: 176 C Yield: 72%

References: [1]Patent: KR2019/33901,2019,A .Location in patent: Paragraph 0218; 0219; 0222; 0223.
[2]Patent: US4057530,1977,A .
[3]Journal of the Chemical Society,1956,p. 1319,1329.
[4]Organic Letters,2013,vol. 15,p. 4266 - 4269.

3
[ 40754-13-0 ]
[ 32566-01-1 ]

Yield	Reaction Conditions	Operation in experiment
58%	With methanesulfonic acid; phosphorus pentoxide; at 80℃; for 0.5h;	Methanesulfonic acid (70 mL) was stirred and heated to 80 oC. Phosphorus pentoxide (9.45 g,66.6 mmol) was added in one portion and the resulting suspension was stirred until ahomogeneous solution was formed (c.a. 5 min). After this time, 43 (7.00 g, 31.1 mmol) wasadded portionwise over 15 minutes. The reaction mixture was stirred at 80 oC for a further 30minutes and then cooled to room temperature an poured over a mixture of crushed ice (c.a.500 g) and sodium hydroxide pellets (45.5 g). A precipitate was formed, which was isolatedby vacuum filtration and washed with water (2 x 20 mL). The residue was purified viarecrystallization from ethanol to afford the title compound 13 as a beige solid (3.75 g, 58 %).The data matched that previously reported in the literature.8Melting point 146-148 oC (ethanol) [lit. 146 oC]; 81H NMR (400 MHz, d6-DMSO) = 11.27 (s, 1H, NH indole), 7.56 (d, J = 7.8 Hz, 1H, HAr),7.45-7.38 (m, 2H, HAr), 7.14-7.07 (m, 2H, HAr), 7.03 (t, J = 7.5 Hz, 1H, HAr), 6.87 (d, J = 8.1Hz, 1H, HAr), 6.75 (m, 2H, H7 and HAr), 5.22 (s, 2H, NH aniline);13C NMR (126 MHz, d6-DMSO) C = 146.1, 136.8, 136.6, 129.3, 129.1, 128.8, 121.5, 120.2,119.5, 117.6, 117.1, 116.2, 111.6, 100.4;FTIR (neat) /cm-1 = 3378, 3304, 3181, 1614, 1490, 1449, 1410, 1347, 1296, 1242, 1154;LRMS (ESI+) 209 ([M + H]+).
	With hydrogenchloride;Zinc chloride; In ammonium hydroxide;	b. Preparation of 2-(2'-amino-phenyl)-indole. An intimate mixture of 10 g (0.045 mol) of 2-amino-acetophenone-phenylhydrazone and 50 g of zinc chloride was heated to about 165 C. After a few minutes a homogeneous brownish liquid was obtained and was mixed and heated for 10 minutes. After standing for 30 minutes at room-temperature, the mixture was taken up with 10% hydrochloric acid and stirred until complete dissolution of the zinc chloride. The yellow suspension obtained was filtered and the crystals were washed with a minimum of cold water and then poured into 100 ml of 10% hydrochloric acid. The reaction medium was heated until a homogenous solution was obtained, after which the solution was filtered. The filtrate was cooled and taken up in ammonia hydrate until precipitation of a whitish substance. The reaction medium was centrifuged and the precipitate was washed several times with cold water. Purification was carried out twice and after two recrystallizations from toluene, 7.5 g of 2-(2'-amino-phenyl)-indole were obtained. M.P.: 156 C Yield: 76%

References: [1]Journal of Organic Chemistry,1994,vol. 59,p. 6777 - 6782.
[2]Synlett,2016,vol. 27,p. 6 - 10.
[3]Journal of the Chemical Society,1956,p. 1319,1329.
[4]Patent: US4057530,1977,A .
[5]European Journal of Organic Chemistry,2009,p. 292 - 303.
[6]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1200 - 1205.
[7]RSC Advances,2018,vol. 8,p. 36980 - 36986.
[8]Advanced Synthesis and Catalysis,2019.
[9]Advanced Synthesis and Catalysis,2019,vol. 361,p. 1414 - 1418.

4
[ 131298-21-0 ]
[ 32566-01-1 ]

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 11835 - 11839.
Angew. Chem.,2013,vol. 125,p. 12051 - 12055,5.
[2]Angewandte Chemie - International Edition,2000,vol. 39,p. 2488 - 2490.
[3]Tetrahedron,2003,vol. 59,p. 1571 - 1587.
[4]Beilstein Journal of Organic Chemistry,2018,vol. 14,p. 2411 - 2417.
[5]Organic and Biomolecular Chemistry,2012,vol. 10,p. 7801 - 7808.
[6]Chemische Berichte,1911,vol. 44,p. 1213.
[7]Chemische Berichte,1911,vol. 44,p. 1213.
[8]Synlett,2008,p. 3006 - 3010.
[9]Journal of Physical Organic Chemistry,2021,vol. 34.

5
[ 32566-01-1 ]
[ 1034-39-5 ]
[ 125187-98-6 ]

References: [1]Tetrahedron,1990,vol. 46,p. 1063 - 1078.
[2]Tetrahedron Letters,1989,vol. 30,p. 2847 - 2850.

6
[ 59050-53-2 ]
[ 32566-01-1 ]

Yield	Reaction Conditions	Operation in experiment
	With tin; at 60℃; for 2h;	General procedure: A mixture of 2-nitroacetophenone 5 (82 mg, 0.5 mmol), corresponding phenylhydrazine 1 (0.5 mmol), and polyphosphoric acid (1.0 g, the P2O5 content of 86%) was stirred at room temperature for 5 min. The process was strongly exothermic. The mixture was then stirred at 60 C until the complete disappearance of the starting reagents (~1.5 h, TLC control). Metallic Sn (1 mmol) was added, the mixture was stored for another 2 h, and the acylating agent (1.2 mmol) was added. The reaction mixture was then heated to 130 C (1,3,5-triazine was used as the synthetic equivalent of HCOOH at 100 C) and stored until the intermediate product disappeared completely (about 2 h). Next,The reaction mixture was cooled to room temperature, diluted with water (40 mL), and neutralized with 20% aqueous ammonia (~7 mL) until basic pH. The resulting mixture was extracted with ethyl acetate (4×15 mL), evaporated, and purifi ed by column chromatography using an acetone-hexane mixture (from 1 : 5to 1 : 1) as the eluent.

References: [1]Synthesis,2010,p. 1386 - 1393.
[2]Journal of the Chemical Society. Perkin transactions I,1983,p. 2417 - 2422.
[3]Russian Chemical Bulletin,2019,vol. 68,p. 836 - 840.
Izv. Akad. Nauk, Ser. Khim.,2019,vol. 68,p. 836 - 840,5.

7
[ 64-18-6 ]
[ 32566-01-1 ]
[ 239-43-0 ]

References: [1]Journal of Organic Chemistry,1994,vol. 59,p. 6777 - 6782.

8
[ 32566-01-1 ]
[ 82453-34-7 ]

References: [1]Il Farmaco,1995,vol. 50,p. 849 - 852.
[2]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 1591 - 1596.

9
[ 32566-01-1 ]
[ 75318-43-3 ]
[ 311330-16-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 2183 - 2185.

10
[ 75-15-0 ]
[ 32566-01-1 ]
[ 382140-31-0 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 6671 - 6674.

11
[ 39785-48-3 ]
[ 32566-01-1 ]
6-(6-methylbenzothiazol-2-yl)indolo[1,2-c]quinazoline [ No CAS ]

References: [1]Tetrahedron,2003,vol. 59,p. 773 - 779.

12
[ 32566-01-1 ]
[ 943-03-3 ]
6-(6-methoxybenzothiazol-2-yl)indolo[1,2-c]quinazoline [ No CAS ]

References: [1]Tetrahedron,2003,vol. 59,p. 773 - 779.

13
[ 32566-01-1 ]
[ 3313-37-9 ]
6-(benzoxazol-2-yl)indolo[1,2-c]quinazoline [ No CAS ]

References: [1]Tetrahedron,2003,vol. 59,p. 773 - 779.

14
[ 32566-01-1 ]
[ 143-33-9 ]
[ 543745-48-8 ]

References: [1]Tetrahedron,2003,vol. 59,p. 1033 - 1048.

15
[ 32566-01-1 ]
[ 536-74-3 ]
6-methyl-6-phenyl-6,11-dihydro-5H-indolo[3,2-c]quinoline [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 17000 - 17006.
[2]European Journal of Organic Chemistry,2010,p. 4719 - 4731.

16
[ 32566-01-1 ]
[ 693-02-7 ]
6-butyl-6-methyl-5,11-dihydro-6<i>H</i>-indolo[3,2-<i>c</i>]quinoline [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 17000 - 17006.

17
EDC (dimethylaminopropyl ethylcarbodiimide hydrochloride) [ No CAS ]
[ 156-38-7 ]
[ 32566-01-1 ]
[ 677297-11-9 ]