[ CAS No. 932-17-2 ] {[proInfo.proName]}

Name: 932-17-2|1-Acetylpyrrolidin-2-one|97%
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 932-17-2 ]

CAS No. :	932-17-2	MDL No. :	MFCD00014101
Formula :	C₆H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YLHUPYSUKYAIBW-UHFFFAOYSA-N
M.W :	127.14	Pubchem ID :	70266
Synonyms :

Safety of [ 932-17-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 932-17-2 ]

* 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 [ 932-17-2 ]

[ 932-17-2 ] Synthesis Path-Downstream 1~46

1
[ 616-45-5 ]
[ 108-22-5 ]
[ 932-17-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; water

Reference： [1]Current Patent Assignee: Eastman Kodak Co. - US2565360, 1951, A

2
[ 616-45-5 ]
[ 108-24-7 ]
[ 932-17-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	for 2h; Heating / reflux;	1 Example 1: Synthesis of i-acetyl-pyrrolidin-2-one:A mixture of 112 g of 2-pyrrolidinone (9) and 249 ml_ of acetic anhydride was heated at reflux for 2 hours. The resultant mixture was allowed to cool to room temperature, was concentrated in vacuo, and was distilled (0.8 mm Hg, 68 0C) to provide 160 g of N-acetyl-2- pyrrolidinone (4) in 96% yield.
96%	for 2h; Reflux;
96%	for 2h; Inert atmosphere; Reflux;

96%	for 2h; Inert atmosphere; Reflux;	1 Preparation of N-Acetylpyrrolidin-2-one (2b) Preparation of N-Acetylpyrrolidin-2-one (2b) N-Acetylpyrrolidin-2-one (2b) was prepared according to a procedure described by MacKenzie and co-workers. (J. Seyden-Penne, Reductions by the Alumino and Borohydrides in Organic Synthesis, 2nd Ed., Wiley-VCH, New York, 1997. G. W. Gribble, Chem. Soc. Rev. 1998, 27, 395.) A mixture of 2-pyrrolidinone (39.3 mmol) and acetic anhydride (78.7 mmol) was added to a 3-neck flask equipped with a magnetic stir bar. The contents of the flask were then heated at reflux for 2 h under Argon. The pale yellow mixture that resulted was then allowed to cool to RT before being concentrated in vacuo. The crude product was then purified by distillation. Yield: 96%
	for 3h; Heating;
	for 1.5h; Heating;
	In tetrahydrofuran for 2h; Reflux;
	for 5h; Reflux;

Reference： [1]Current Patent Assignee: GENERAL ELECTRIC CO - WO2006/75226, 2006, A1 Location in patent: Page/Page column 21
[2]Tian, Fengtao; Yao, Dongmei; Liu, Yuanyuan; Xie, Fang; Zhang, Wanbin [Advanced Synthesis and Catalysis, 2010, vol. 352, # 11-12, p. 1841 - 1845]
[3]John, Jeremy M.; Bergens, Steven H. [Angewandte Chemie - International Edition, 2011, vol. 50, # 44, p. 10377 - 10380]
[4]Current Patent Assignee: UNIVERSITY OF ALBERTA - US2014/163225, 2014, A1 Location in patent: Paragraph 0181
[5]Hall et al. [Journal of the American Chemical Society, 1958, vol. 80, p. 6420,6421]
[6]Ananthapadmanabhan, S.; Raja, T. K.; Srinivasan, V.; Simon, A. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, p. 580]
[7]Irvine, Mark W.; Patrick, Graham L.; Kewney, Justin; Hastings, Stuart F.; MacKenzie, Simon J. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 2032 - 2037]
[8]Jung, Kwan-Young; Samadani, Ramin; Chauhan, Jay; Nevels, Kerrick; Yap, Jeremy L.; Zhang, Jun; Worlikar, Shilpa; Lanning, Maryanna E.; Chen, Lijia; Ensey, Mary; Shukla, Sagar; Salmo, Rosene; Heinzl, Geoffrey; Gordon, Caryn; Dukes, Troy; MacKerell Jr., Alexander D.; Shapiro, Paul; Fletcher, Steven [Organic and Biomolecular Chemistry, 2013, vol. 11, # 22, p. 3706 - 3732]
[9]Wang, Tiantian; Dong, Shiyang; Chen, Xiaodong; Qian, Kun; Wang, Huayu; Quan, Hexiu; Zhang, Zhongli; Zuo, Yueming; Huang, Liping; Li, Dongxun; Yang, Ming; Yang, Shilin; Jin, Yi; Wang, Zengtao [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 8, p. 1324 - 1329]

3
[ 98-01-1 ]
[ 932-17-2 ]
[ 53031-79-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In tetrahydrofuran at 10 - 14℃;

Reference： [1]Bose,A.K. et al. [Tetrahedron, 1974, vol. 30, p. 3 - 9]

4
[ 98-03-3 ]
[ 932-17-2 ]
[ 53031-78-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In tetrahydrofuran at 10 - 14℃;

Reference： [1]Bose,A.K. et al. [Tetrahedron, 1974, vol. 30, p. 3 - 9]

5
[ 120-57-0 ]
[ 932-17-2 ]
[ 1859-42-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride

Reference： [1]Zimmer,H. et al. [Journal of Heterocyclic Chemistry, 1965, vol. 2, p. 171 - 175]

6
[ 932-17-2 ]
[ 95-92-1 ]
[ 92377-70-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol In toluene

Reference： [1]Buechel,K.H.; Korte,F. [Chemische Berichte, 1962, vol. 95, p. 2453 - 2459]

7
[ 616-45-5 ]
[ 75-36-5 ]
[ 932-17-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran for 0.5h; Ambient temperature; Yield given;

Reference： [1]Sasaki; Mori; Nakamura; Shibasaki [Journal of Medicinal Chemistry, 1991, vol. 34, # 2, p. 628 - 633]

8
[ 2687-91-4 ]
[ 2314-78-5 ]
[ 932-17-2 ]

Reference： [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 975 - 979
[2]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 975 - 979

9
[ 4030-18-6 ]
[ 932-17-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With pyridine; N-hydroxyphthalimide; sodium perchlorate In acetonitrile controlled potential electrolysis, electrodes: glassy-carbon vs. SCE;
51%	Stage #1: N-(acetyl)pyrrolidine With [bis(acetoxy)iodo]benzene In nitromethane at 0℃; Stage #2: With tert.-butylhydroperoxide In decane; nitromethane at 0 - 25℃; for 18h;
0.9 mmol	With oxygen; titanium(IV) oxide In water for 48h; Irradiation;

Reference： [1]Masui, Masaichiro; Hara, Seijiro; Ozaki, Shigeko [Chemical and pharmaceutical bulletin, 1986, vol. 34, # 3, p. 975 - 979]
[2]Zhao, Yi; Ang, Jascelyn Qian Lin; Ng, Angela Wan Ting; Yeung, Ying-Yeung [RSC Advances, 2013, vol. 3, # 43, p. 19765 - 19768]
[3]Pavlik, James W.; Tantayanon, Supawan [Journal of the American Chemical Society, 1981, vol. 103, # 22, p. 6755 - 6757]

10
[ 872-85-5 ]
[ 932-17-2 ]
(E)-3-pyridin-4-ylmethylene-pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride 1.) THF, 5 deg C, 2.) THF, from 5 deg C to RT; Yield given. Multistep reaction;

Reference： [1]Andreani; Rambaldi; Locatelli; Leoni; Bossa; Chiericozzi; Galatulas; Salvatore [European Journal of Medicinal Chemistry, 1993, vol. 28, # 10, p. 825 - 829]

11
[ 932-17-2 ]
[ 123-11-5 ]
(E)-3-(4-methoxybenzylidene)pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride 1.) THF, 5 deg C, 2.) THF, from 5 deg C to RT; Yield given. Multistep reaction;

Reference： [1]Andreani; Rambaldi; Locatelli; Leoni; Bossa; Chiericozzi; Galatulas; Salvatore [European Journal of Medicinal Chemistry, 1993, vol. 28, # 10, p. 825 - 829]

12
[ 932-17-2 ]
[ 93-02-7 ]
(E)-3-(2,5-dimethoxybenzylindene)pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride 1.) THF, 5 deg C, 2.) THF, from 5 deg C to RT; Yield given. Multistep reaction;

Reference： [1]Andreani; Rambaldi; Locatelli; Leoni; Bossa; Chiericozzi; Galatulas; Salvatore [European Journal of Medicinal Chemistry, 1993, vol. 28, # 10, p. 825 - 829]

13
[ 932-17-2 ]
[ 872-32-2 ]

Yield	Reaction Conditions	Operation in experiment
	With calcium oxide Heating; Yield given;

Reference： [1]Ananthapadmanabhan, S.; Raja, T. K.; Srinivasan, V.; Simon, A. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, p. 580]

14
1-(2-Methoxy-acetyl)-pyrrolidin-2-one [ No CAS ]
[ 616-45-5 ]
[ 7486-88-6 ]
[ 932-17-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 9% 2: 18% 3: 12%	In acetonitrile for 2h; Irradiation; other semicyclic imides, various solvents;

Reference： [1]Machida, Minoru; Takechi, Haruko; Sakushima, Akiyo; Kanaoka, Yuichi [Heterocycles, 1981, vol. 15, # 1, p. 479 - 480]

15
[ 932-17-2 ]
1-acetyl-5-fluoro-2-pyrrolidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With Et₃N*4HF In acetonitrile at -45℃; Electrochemical reaction;

Reference： [1]Sawaguchi, Masanori; Hara, Shoji; Fukuhara, Tsuyoshi; Yoneda, Norihiko [Israel Journal of Chemistry, 1999, vol. 39, # 2, p. 151 - 154]

16
[ 183208-72-2 ]
[ 932-17-2 ]

Yield	Reaction Conditions	Operation in experiment
40%	With oxygen; copper dichloride In hydrogenchloride; acetonitrile for 24h;

Reference： [1]Doan, Huynh Dong; Gore, Jacques; Vatele, Jean-Michel [Tetrahedron Letters, 1999, vol. 40, # 37, p. 6765 - 6768]

Yield	Reaction Conditions	Operation in experiment
	Rk. m. Oxalsaeure-diethylester, Kalium-pulver, in Ae. + etwas abs. A., 0-10grad Bildung N-Acetyl-3-ethoxalyl-pyrrolidon-(2) neben 3-Ethoxalyl-pyrrolidon-(2);
	Rk. m. Oxalsaeure-diethylester, Kalium-pulver, in Toluol, 100grad Bildung N,N'-Oxalyl-bis-(4-amino-buttersaeure-ethylester) u. 2,3-Dioxo-4-ethoxycarbonyl-pyrrolidin;
	Hydrolyse;

	Hydrolyse: ΔH, ΔS;
	Rk. m. Benzaldehyd;
	Rk. m. 3,4-Dimethoxybenzaldehyd u. a.;
	Rk. mit Benzaldehyd;
	Rk. mit 3,4-Dimethoxybenzaldehyd (u.a.);
	Rk. m. Anilin, in THF, 90grad, 16-48 h Bildung Acetanilid u. Pyrrolid-2-on;
	Rk. m. Benzylamin, in THF, 70grad, 16-48 h Bildung N-Benzyl-acetamid u. Pyrrolid-2-on;
	Rk. m. 1. Isonicotinsaeure-ethylester, Kalium, in Bzl. 2. wss. HCl, Hydrolyse Bildung 3-Isonicotinoyl-2-pyrrolidon u. Isoncotinoyl-essigsaeure-ethylester;

Yield	Reaction Conditions	Operation in experiment
	at 20℃; Hydrolysis;

Yield	Reaction Conditions	Operation in experiment
	2-Pyrrolidon, Acetanhydrid, Δ;
	Pyrrolid-2-on, Acetylchlorid, Triethylamin, in Bzl.;
	Pyrrolid-2-on, Acetanhydrid, Acetylchlorid;

	Acetanhydrid, N-Kalium-2-pyrrolidon;
	2-Pyrrolidon, Ac2O;
	DBF, Δ;
	1-Acetyl-pyrrolidin, Benzophenon, O2, h.ν;

20
[ 108-24-7 ]
[ 932-17-2 ]

Reference： [1]Tafel; Stern [Chemische Berichte, 1900, vol. 33, p. 2235]

Yield	Reaction Conditions	Operation in experiment
	elektrolytische Reduktion;

22
[ 5264-35-7 ]
[ 201230-82-2 ]
[ 932-17-2 ]

Yield	Reaction Conditions	Operation in experiment
96 % Chromat.	In 1,2-dimethoxyethane at 100℃; for 48h;

Reference： [1]Xu, Hongyu; Jia, Li [Organic Letters, 2003, vol. 5, # 21, p. 3955 - 3957]

23
[ 932-17-2 ]
[ 135-02-4 ]
[ 1859-44-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In tetrahydrofuran

Reference： [1]Current Patent Assignee: MITSUBISHI CHEMICAL HOLDINGS CORPORATION - EP1188747, 2002, A1 Location in patent: Page 164

24
[ 865203-77-6 ]
[ 932-17-2 ]
[ 198204-95-4 ]

Yield	Reaction Conditions	Operation in experiment
33%	With sodium hydride In tetrahydrofuran at 0℃; for 4.5h;	12 Preparation 12: General Aldol Procedure 1; 3-f 5-Fluoro-2- (4-methvl-piperazin-1-vl)-benzvl idenel-pyrrol idin-2-one; A solution of 9.0 g (40.5 mmol) of 5-Fluoro-2- (4-methyl-piperazin-1-yl)-benzaldehyde and 5.1 g (40.5 mmol) of N-acetylpyrrolidinone in 80 mL of tetrahydrofuran is slowly added to a 0 °C solution of 5.4 g (133.6 mmol) of sodium hydride in 80 mL of tetrahydrofuran over a 2 hour period. After 2.5 hour at 0 °C, the reaction is quenched with sat. ammonium chloride and extracted with methylene chloride. The organic layer is dried with magnesium sulfate and concentrated to provide a yellow solid. Recrystallization from ethyl acetate and diispropyl ether provided 3.92 g (33%) of 3- [5-Fluoro-2- (4-methyl-piperazin-1-yl)-benzylidene]-pyrrolidin-2-one as a white solid. Diagnostic C13 NMR (100 MHz, CDCI3) 26.4, 39.9, 46.1, 52.9, 55.3, 115.2, 115.5, 115. 8, 116. 0,120. 2, 120. 3, 126. 7, 131. 1,148. 9, 157. 3, 159. 7, 172. 8; MS m/z 290. 3 (M+1)

Reference： [1]Current Patent Assignee: PFIZER INC - WO2005/90300, 2005, A1 Location in patent: Page/Page column 32

25
[ 872882-89-8 ]
[ 932-17-2 ]
[ 872882-90-1 ]

Yield	Reaction Conditions	Operation in experiment
37%	With sodium hydride In tetrahydrofuran at 0 - 20℃; for 18.6667h;	2 A solution of 10.0 g (49 mmol) of 2-(4-methyl-piperazin-1-yl)-pyridine-3-carbaldehyde and 6.2 g (49 mmol) of N-acetylpyrrolidinone in 100 mL of tetrahydro-furan was slowly added to a 0° C. suspension of 6.45 g (161 mmol, 60% by weight) of sodium hydride in 100 mL of tetrahydrofuran over a 30 minute period. After the addition was complete, the mixture was stirred 10 min at 0° C. and then stirred at room temperature for 18 h. The reaction mixture was quenched into water and extracted with methylene chloride. The organic layer was dried with sodium sulfate and concentrated to provide a yellow solid. Recrystallization from ethyl acetate provided 4.9 g (37% yield) of the title compound as a white solid. MS (AP/CI) 273.3 (M+H). 13C NMR (100 MHz, CDCl3) 26.3, 39.9, 46.3, 50.4, 55.3, 116.7, 121.7, 127.2, 130.8, 137.0, 147.7, 161.3, 172.6.

Reference： [1]Current Patent Assignee: PFIZER INC - US2006/25421, 2006, A1 Location in patent: Page/Page column 13

26
[ 932-17-2 ]
[ 112253-26-6 ]
3-[2-(4-benzyl-piperazin-1-yl)-benzylidene]-pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With sodium hydride In tetrahydrofuran at 0 - 35℃; for 3h;	3 Example 3: Synthesis of 1-[4-(1-methoxy-1-methyl-ethyl)-phenvn-3-(2-piperazin- 1-yl-bertzvD-pyrrolidin-2-one (compound 12): EPO 12A mixture of 25 g of benzylpiperazine (1) and 10 g of 2-fluorobenzaldehyde (2) were allowed to react in refluxing dioxane/water (1 :2, 90 mL total volume) for 24 hours in the presence of 17 g K2CO3. The resultant reaction mixture was allowed to cool to room temperature, was extracted with methylene chloride and the organic layer was then washed with water, 5% hydrochloric acid, brine, and was then dried over magnesium sulfate, was filtered, and the solvent was removed in vacuo. Purification by silica gel chromatography (5:1 hexanes-ethyl acetate) afforded 20 g of the benzaldehyde 3 in 89% yield; MS (AP/CI) observed: 281.1 (M+H)+ (100%). The benzaldehyde 3 (8 g) was subsequently allowed to react with 7.3 g of 1-acetyl-pyrrolidin-2-one (4) in the presence of 4.6 g of NaH (60% in mineral oil) at O0C for 1 hour followed by warming to room temperature and stirring for 2 hours. After quenching carefully with methanol at 0 0C, the solvent was removed in vacuo, the residue was diluted with water, was extracted with methylene chloride and the organic extracts were washed with brine and were dried over magnesium sulfate and were filtered. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (40:1 chloroform-methanol) to provide 7.9g of 3-[2-(4-benzyl-piperazin-1-yl)-benzylidene]- pyrrolidin-2-one (5) in 80% yield; MS (AP/CI) observed: 348.1 (M+H)+, 100%. Hydrogenation of 6.3 g of 5 with 1.5 g of Pd/C in 100 mL of methanol under 50 p.s.i. of pressure at 600C provided 3.8 g (82% yield) of 3-(2-piperazin-1-yl-benzyl)-pyrrolidin-2-one (6) following filtration, removal of solvent in vacuo, and purification by silica gel chromatography (30:1 :0.3 chloroform-methanol-ammonium hydroxide); MS (AP/CI) observed: 260.1 (M+H)+, 100%.3-(2-Piperazin-1-yl-benzyl)-pyrrolidin-2-one (6) (1.2 grams) was subsequently allowed to react with 1.27 g of 1-bromo-4-(1-methoxy-1-methyl-ethyl)-benzene (11) in the presence of 0.041 grams of N,N'-dimethylethylenediamine, 0.088 g of CuI and 0.96 grams of K2CO3 in toluene (6 mL) at 110 °C for 17 hours to provide 1.2 grams of the racemate 1-[4-(1-methoxy- 1-methyl-ethyl)-phenyl]-3-(2-piperazin-1-yl-benzyl)-pyrrolidin-2-one (12) (64% yield) following silica gel chromatography (40:1 :0.5 chloroform-methanol-ammonium hydroxide); MS (AP/CI) observed: 408.2 (M+H)+.

Reference： [1]Current Patent Assignee: GENERAL ELECTRIC CO - WO2006/75226, 2006, A1 Location in patent: Page/Page column 23

27
[ 932-17-2 ]
[ 135-02-4 ]
(E)-3-(2-methoxybenzylidene)pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran	(S)-3-(2'-(2-hydroxy-3-(4-(5,6,7,8-tetrahydronaphthalen-2-yl) piperidino)propyloxy)benzylidene)-2-pyrrolidone 1/4 hydrate (S)-3-(2'-(2-hydroxy-3-(4-(5,6,7,8-tetrahydronaphthalen-2-yl) piperidino)propyloxy)benzylidene)-2-pyrrolidone 1/4 hydrate Sodium hydride (16 g) was suspended in tetrahydrofuran (100 ml) and a solution of N-acetylpyrrolidone (25 g) and o -anisaldehyde (26.8 g) in tetrahydrofuran (100 ml) was added dropwise under ice-cooling. After completion of the reaction, the reaction mixture was poured into water. The mixture was acidified with hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure to give oily 3-(2'-methoxybenzylidene)-2-pyrrolidone (4.7 g). The oil was dissolved in methylene chloride (60 ml).

Reference： [1]Current Patent Assignee: MITSUBISHI CHEMICAL HOLDINGS CORPORATION - US2002/111358, 2002, A1

28
[ 932-17-2 ]
[ 105-07-7 ]
3-(4-cyanobenzylidene)-2-pyrrolidone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; methanol; dichloromethane	N 3-[4-(2-Oxazolin-2-yl)benzylidene]pyrrolidine EXAMPLE N 3-[4-(2-Oxazolin-2-yl)benzylidene]pyrrolidine A solution of 5.0 g of N-acetyl-2-pyrrolidone and 5.17 g of 4-cyanobenzaldehyde in 50 ml of tetrahydrofuran is added dropwise to a suspension of 5.36 g of sodium hydride (55% in oil) in 50 ml of tetrahydrofuran at 5°-10° C. and the mixture is then stirred at 0° C. for 1 hour. Excess sodium hydride is eliminated by the addition of some methanol, and the reaction mixture is poured onto ice and neutralized with glacial acetic acid. The precipitate is suction-filtered and dissolved in a methylene chloride/methanol mixture, and the solution is dried and evaporated down. The residue is triturated with ether and suction-filtered. 1.4 g of 3-(4-cyanobenzylidene)-2-pyrrolidone are obtained as a colourless powder of melting point 260° C.

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - US5466687, 1995, A

29
[ 127329-65-1 ]
[ 932-17-2 ]
3-[(7-chloro-3,4,5,6-tetrahydro-4-methylfuro[4,3,2-ef][3]benzazepin-2-yl)methylene]-2-pyrrolidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; methanol; mineral oil	7 3-[(7-Chloro-3,4,5,6-tetrahydro-4-methylfuro[4,3,2-ef][3]benzazepin-2-yl)methylene]-2-pyrrolidinone EXAMPLE 7 3-[(7-Chloro-3,4,5,6-tetrahydro-4-methylfuro[4,3,2-ef][3]benzazepin-2-yl)methylene]-2-pyrrolidinone A solution of N-acetyl-2-pyrrolidinone (0.48 g, 3.8 mmol) and 7-chloro-3,4,5,6-tetrahydro-4-methylfuro[4,3,2-ef][3]benzazepine-2-carboxaldehyde (0.95 g, 3.8 mmol; U.S. Pat. No. 4,959,360) in tetrahydrofuran (15 ml) was added dropwise to a suspension of sodium hydride (50% in mineral oil, 0.54 g, 11.3 mmol) in tetrahydrofuran (35 ml) stirred in an ice bath at a rate that maintained internal temperature between 5°-10° C. The mixture was stirred at 5° C. for 1 h, treated with methanol (2 ml) and concentrated. The residue was partitioned between methylene chloride and 3N hydrochloric acid, and the aqueous phase was basified to pH 8.5 with ammonium hydroxide and extracted with methylene chloride and chloroform. The organic phase was washed with water, dried with sodium sulfate and concentrated to give a solid that was crystallized from chloroform. The mother liquor was concentrated and the residue purified by thin layer chromatography on silica gel eluted with methanol-chloroform (10:90).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US5599810, 1997, A

30
[ 5160-65-6 ]
[ 932-17-2 ]
manganese(ll) chloride [ No CAS ]
Mn⁽²⁺⁾*3C₆H₉NO₂*2SbCl₆^(1-)=Mn(C₆H₉NO₂)3(SbCl₆)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In nitromethane stirring mixt. of educts at room temp. for 24 h; filtering, evapn. in vac.; washing with n-pentane in dry atmosphere;

Reference： [1]Driessen, W. L.; Everstijn, P. L. A. [Journal of Coordination Chemistry, 1980, vol. 10, p. 155 - 158] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Mn: MVol.D3, 16.1.3.2, page 79 - 79]

31
Mn⁽²⁺⁾*6CH₃NO₂*2SbCl₆^(1-)=[Mn(CH₃NO₂)6](SbCl₆)2 [ No CAS ]
[ 932-17-2 ]
Mn⁽²⁺⁾*3C₆H₉NO₂*2SbCl₆^(1-)=Mn(C₆H₉NO₂)3(SbCl₆)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In nitromethane

32
[ 932-17-2 ]
[ 120-14-9 ]
[ 1859-52-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In tetrahydrofuran at 0 - 10℃;

Reference： [1]Irvine, Mark W.; Patrick, Graham L.; Kewney, Justin; Hastings, Stuart F.; MacKenzie, Simon J. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 2032 - 2037]

33
[ 932-17-2 ]
[ 67387-76-2 ]
C₁₇H₂₁NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In tetrahydrofuran at 0 - 10℃;

Reference： [1]Irvine, Mark W.; Patrick, Graham L.; Kewney, Justin; Hastings, Stuart F.; MacKenzie, Simon J. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 2032 - 2037]

34
[ 932-17-2 ]
[ 100-52-7 ]
(E)-3-phenylmethylene-2-pyrrolidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With sodium hydride In mineral oil at 0 - 20℃;

Reference： [1]Tian, Fengtao; Yao, Dongmei; Liu, Yuanyuan; Xie, Fang; Zhang, Wanbin [Advanced Synthesis and Catalysis, 2010, vol. 352, # 11-12, p. 1841 - 1845]

35
[ 932-17-2 ]
[ 616-45-5 ]
[ 75694-83-6 ]

Yield	Reaction Conditions	Operation in experiment
	With trans-[RuH₂((R)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl)((R,R)-1,2-diphenylethylenediamine)]; hydrogen; potassium hexamethylsilazane In tetrahydrofuran at 80℃; for 16h; Autoclave;
	With trans-[Ru((R)-BINAP)(H)2((R,R)-dpen)]; hydrogen; potassium hexamethylsilazane at 80℃;	4 The reactivity of (1) was low to moderate. Compound (2a) was hydrogenated in only 27 turnovers (TO) to give the ring-opened N-methanesulfonyl amino alcohol product with 2 mol % Ru in THF (100° C., 50 atm, 20 mol % KOtBu, 39 h). Compound (2b) formed mixtures of pyrrolidine-2-one (major) and the ring-opened N-acetyl amino alcohol in 45 TO using 2 mol % Ru (80° C., 50 atm H2, 20 mol % KN[Si(CH3)3]2, 16 h). N-phenylpyrrolidin-2-one (2c) did not react under these conditions.

Reference： [1]John, Jeremy M.; Bergens, Steven H. [Angewandte Chemie - International Edition, 2011, vol. 50, # 44, p. 10377 - 10380]
[2]Current Patent Assignee: UNIVERSITY OF ALBERTA - US2014/163225, 2014, A1 Location in patent: Paragraph 0248; 0249; 0250

36
[ 75694-83-6 ]
[ 932-17-2 ]

Yield	Reaction Conditions	Operation in experiment
35%	With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II); N,N'-(3,3'-bis(propyl)methylamine)bis(salicylideneiminato)cobalt(II); 2,6-dimethoxy-p-quinone In toluene at 100℃; for 18h;

Reference： [1]Babu, Beneesh P.; Endo, Yoshinori; Baeckvall, Jan-E. [Chemistry - A European Journal, 2012, vol. 18, # 37, p. 11524 - 11527,4]

37
[ 932-17-2 ]
[ 10031-82-0 ]
[ 1438408-89-9 ]

Yield	Reaction Conditions	Operation in experiment
45%	With potassium <i>tert</i>-butylate In tetrahydrofuran at 55℃; for 1h;

Reference： [1]Jung, Kwan-Young; Samadani, Ramin; Chauhan, Jay; Nevels, Kerrick; Yap, Jeremy L.; Zhang, Jun; Worlikar, Shilpa; Lanning, Maryanna E.; Chen, Lijia; Ensey, Mary; Shukla, Sagar; Salmo, Rosene; Heinzl, Geoffrey; Gordon, Caryn; Dukes, Troy; MacKerell Jr., Alexander D.; Shapiro, Paul; Fletcher, Steven [Organic and Biomolecular Chemistry, 2013, vol. 11, # 22, p. 3706 - 3732]

38
[ 88-12-0 ]
[ 932-17-2 ]

Yield	Reaction Conditions	Operation in experiment
75 %Chromat.	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; dihydrogen peroxide; nitric acid In N,N-dimethyl acetamide at 55℃; for 1h; Green chemistry;

Reference： [1]Kon, Yoshihiro; Tanaka, Shinji; Nakashima, Takuya; Sato, Kazuhiko; Shimada, Hiromichi [Journal of the Chinese Chemical Society, 2014, vol. 61, # 7, p. 749 - 756]

39
[ 692-33-1 ]
[ 201230-82-2 ]
[ 932-17-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With bis[2-(diphenylphosphino)phenyl] ether; palladium(II) iodide In toluene at 105℃; for 20h; Inert atmosphere; Autoclave; regioselective reaction;

Reference： [1]Li, Haoquan; Dong, Kaiwu; Neumann, Helfried; Beller, Matthias [Angewandte Chemie - International Edition, 2015, vol. 54, # 35, p. 10239 - 10243][Angew. Chem., 2015, vol. 127, # 35, p. 10377 - 10381,5]

40
[ 24424-99-5 ]
2-formyl-4-methoxyphenyl-4-acetamidobutanoate [ No CAS ]
[ 932-17-2 ]
C₁₉H₂₃NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap In acetonitrile at 20℃; for 24h; Overall yield = 230 mg;	N-(2-(6-Methoxy-2-oxo-2H-chromen-3-yl)ethyl)acetamide (5) Intermediate 12 (500 mg, 1.79 mmol), di-tert-butyldicarbonate (Boc2O, 699 mg, 1.79 mmol) and DMAP (547 mg, 2.69 mmol) were dissolved in anhydrous acetonitrile (MeCN, 5.5 mL). The mixture was stirred at rt for 24h. The solvent was removed to afford a crude that was chromatographed (hexane : EtOAc) to give 230 mg of a mixture of Boc-protected-5 (HPLC-MS (m/z) [MH+] 362.35, Amax 286 nm) and 1-acetylpyrrolidin-2-one (HPLC-MS (m/z), [MH+] 127.79, no abs. 230 to 400 nm) in a proportion of ca. 1:2 as determined by 1H-NMR. This mixture was dissolved in triethylsilane (253 μL, 1.6 mmol), treated at 0 °C with trifluoroacetic acid (TFA) and DCM (1.8 mL, 1:2) and then, allowed to reach rt. After 90 min the reaction was finished and DCM partially removed. The mixture was then added over a cooled sat. solution of ammonia in MeOH (6 mL). Solvent and excess of ammonia were removed under vacuum and the solid mixture of salts and organics chromatographed (DCM : MeOH) to afford 5 (40 mg, 9% two steps) as a yellow shiny solid of mp 205 - 208 °C. HPLC purity 95% (230 to 400 nm). 1H NMR (500 MHz, DMSO-d6) δ 9.66 (s, 1H), 7.71 (t, J = 2.9 Hz, 1H), 6.95 (d, J = 2.4 Hz, 1H), 6.87 - 6.83 (m, 2H), 3.72 (d, J = 7.2 Hz, 2H), 3.70 (s, 3H), 3.02 (td, J = 7.2, 2.9 Hz, 2H), 2.46 (s, 3H). 13C NMR (126 MHz, DMSO-d6) δ 171.30, 169.04, 152.32, 151.42, 130.43, 128.43, 122.33, 117.69, 116.93, 113.52, 55.81, 42.56, 25.21, 22.89. HRMS (ESI+): m/z calcd for C14H15NO4 (M)+ 261.1001, found 261.0995.

Reference： [1]De La Fuente Revenga, Mario; Herrera-Arozamena, Clara; Fernández-Sáez, Nerea; Barco, Gema; García-Orue, Itxaso; Sugden, David; Rivara, Silvia; Rodríguez-Franco, María Isabel [European Journal of Medicinal Chemistry, 2015, vol. 103, p. 370 - 373]

41
[ 3025-96-5 ]
[ 932-17-2 ]
C₁₉H₂₃NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 5 h / 20 °C 2: dmap / acetonitrile / 24 h / 20 °C

42
[ 932-17-2 ]
4-((2-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)thiazol-4-yl)methoxy)-3-fluorobenzaldehyde [ No CAS ]
(E)-3-(4-((2-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)thiazol-4-yl)methoxy)-3-fluorobenzylidene)pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With potassium <i>tert</i>-butylate In tetrahydrofuran at 55℃; for 5h; Inert atmosphere;	(E)-3-(4-((2-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)thiazol-4-yl)methoxy)-3-fluorobenzylidene)pyrrolidin-2-one (26). Compound19(300 mg, 0.70 mmol) andN-acetylpyrrolidin-2-one (98 mg, 0.77 mmol) were dissolved in THF and potassiumtert-butoxide (102 mg, 0.92 mmol) was added to the reaction flask. The reaction mixture was stirred at 55for 5 h. The reaction mixture was diluted with EtOAc and washed with sat’d NaHCO3aqueous solution. The organic layer was collected, dried over anhydrous Na2SO4, filtered and concentrated. Product was obtained by recrystallization in the presence of MeOH and washed with MeOH (2 x 5 mL), and dried under vacuo to afford the compound 26 (160 mg, 46%) with light yellow solid.1H-NMR (CDCl3, 300 MHz) δ 8.21 (2H, s, pyrimidine), 7.29-7.25 (4H, m, Ar), 7.22 (1H, d,J= 6.3 Hz, Ar), 7.12 (1H, t,J= 6.6 Hz, Ar), 6.30 (1H, bs, NH), 5.29 (2H, s, OCH2), 4.86 (2H, d,J= 10.6 Hz, CH2), 3.60 (2H, t,J= 10.5 Hz, CH2), 3.31 (1H, tt,J= 15.1 Hz, 3.0 Hz, CH), 3.15 (2H, t,J= 10.3 Hz, CH2), 3.04 (2H, t,J= 15.3 Hz, CH2), 2.50 (2H, q,J= 10.0 Hz, CH2), 2.22 (2H, d,J= 10.0 Hz, CH2), 1.80 (2H, dq,J= 9.7 Hz, 2.4 Hz, CH2), 1.22 (3H, t,J= 9.7 Hz, CH3).

Reference： [1]Kim, Hyojin; Cho, Suk Joon; Yoo, Minjin; Kang, Seung Kyu; Kim, Kwang Rok; Lee, Hwan Hee; Song, Jin Sook; Rhee, Sang Dal; Jung, Won Hoon; Ahn, Jin Hee; Jung, Jae-Kyung; Jung, Kwan-Young [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 23, p. 5213 - 5220]

43
[ 120-57-0 ]
[ 932-17-2 ]
(E)-3-(benzo[d][1,3]-dioxol-5-ylmethylene)pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid In tetrahydrofuran at 0 - 55℃; for 24h;

Reference： [1]Wang, Tiantian; Dong, Shiyang; Chen, Xiaodong; Qian, Kun; Wang, Huayu; Quan, Hexiu; Zhang, Zhongli; Zuo, Yueming; Huang, Liping; Li, Dongxun; Yang, Ming; Yang, Shilin; Jin, Yi; Wang, Zengtao [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 8, p. 1324 - 1329]

44
[ 159981-19-8 ]
[ 932-17-2 ]
3-[1-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]meth-(E)-ylidene]pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a suspension of NaH (2.0 g) in THF (100 mL) was added a mixture of 1-acetyl-pyrrolidin-2-one (1.6 g), <strong>[159981-19-8]6-(2,2,2-trifluoro-ethoxy)-pyridine-3-carbaldehyde</strong> (2.6 g) and THF (5 mL) dropwise at ice-bath temperature. After the addition was complete, the reaction mixture was stirred for 10 min at ice-bath temperature. Acetic acid (5 mL) was slowly added dropwise to destroy the excess NaH. The reaction mixture was poured into ice-water and extracted with EA (100 mL*2). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by SGC (DCM/MeOH=20:1) to provide 3-[1-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-meth-(E)-ylidene]-pyrrolidin-2-one. MS ESI+: m/z=273 [M+H]+.

Reference： [1]Patent: US2018/237419,2018,A1 .Location in patent: Paragraph 0253

45
[ 521984-95-2 ]
[ 932-17-2 ]
(E)-3-((1-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)methylene)pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	Stage #1: 1-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde With lithium diisopropyl amide In tetrahydrofuran at 20℃; for 1h; Cooling with ice; Inert atmosphere; Stage #2: N-acetylpyrrolidinone In tetrahydrofuran at 45℃; for 48h; Inert atmosphere;	Step A: (E)-3-((1-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)methylene)pyrrolidin-2-one (15a) To a solution of compound 3a (590 mg, 2.5 mmol) in THF (30 mL) in ice-water bath was added LDA (2 M in THF, 2.5 mL, 5 mmol) dropwise. After the reaction mixture was warmed to room temperature for 1 h, 1-acetylpyrrolidin-2-one (1.27 g, 10 mmol) was slowly added. The resulting mixture was stirred at 45 °C for 48 h. The mixture was quenched with sat. aqueous NH4Cl solution (3 mL), diluted with water (50 mL) and extracted with EtOAc (3×50 mL). The combined organic layers was washed with brine, dried over Na2SO4 and concentrated to give the crude, which was purified with flash chromatography [MeOH:DCM = 1:10] to give compound 15a ( 450 mg, 59 %) as a white foamed solid; 1H NMR (400 MHz, CDCl3) δ 8.42 (dd, J = 4.7, 1.4 Hz, 1H), 8.03 (dd, J = 7.9, 1.4 Hz, 1H), 7.61 - 7.37 (m, 6H), 7.18 (dd, J = 7.9, 4.7 Hz, 1H), 6.86 (s, 1H), 3.82 (s, 3H), 3.32 (t, J = 6.6 Hz, 2H), 2.47 - 2.27 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 172.9, 148.4, 143.4, 141.3, 131.0, 130.6, 128.9, 128.8, 128.0, 123.1, 119.7, 116.5, 108.5, 39.7, 29.9, 26.9.

Reference： [1]Hu, Wenhui; Lan, Huiyao; Lian, Guangyu; Sheng, Jingyi; Wu, Dan; Wu, Nannan; Yang, Zhongjin; Yu, Xiyong [Bioorganic and medicinal chemistry letters, 2020, vol. 30, # 17]

46
[ 521984-95-2 ]
[ 932-17-2 ]
C₁₉H₁₇N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	Stage #1: 1-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde With lithium diisopropyl amide In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: N-acetylpyrrolidinone In tetrahydrofuran at 45℃; for 48h;	5 Synthesis of Intermediate 15a At 0 °C, a THF solution of LDA (18.2 mL, 36.4 mmol) was added dropwise to a solution of 3c (4.3 g, 18.2 mmol) in THF (30 mL), warm up to room temperature and stir for 1 hour, add 1-acetylpyrrolidin-2-one (9.25 g, 72.9 mmol), and stir at 45 °C for 48 hours. The reaction of the sampling point plate is basically completed and quenched by adding saturated NaHCO3.Dilute with NH4Cl (3mL) and water (50mL), extract with EA, wash with saturated brine (50mL), dry with anhydrous Na2SO4, concentrate, and purify by silica gel column chromatography to obtain white solid compound 15a (2.3mg, 42%)

Reference： [1]Current Patent Assignee: GUANGZHOU MEDICAL UNIV NEW DRUG MANUFACTURING; GUANGZHOU MEDICAL UNIVERSITY - CN111606904, 2020, A Location in patent: Paragraph 0218-0221

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
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H242	Heating may cause a fire
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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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Health hazards
Code	Phrase
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H301	Toxic if swallowed
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H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 932-17-2 ] {[proInfo.proName]}

Quality Control of [ 932-17-2 ]

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[ 932-17-2 ] Synthesis Path-Downstream 1~46

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Amides

Related Parent Nucleus of [ 932-17-2 ]

Pyrrolidines

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[ 932-17-2 ]

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[ 932-17-2 ]