[ CAS No. 119-68-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 119-68-6 * Storage: {[proInfo.prStorage]}

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 119-68-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 119-68-6 ]

SDS Specification

Alternatived Products of [ 119-68-6 ]

Product Details of [ 119-68-6 ]

CAS No. :	119-68-6	MDL No. :	MFCD00002424
Formula :	C₈H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WVMBPWMAQDVZCM-UHFFFAOYSA-N
M.W :	151.16	Pubchem ID :	67069
Synonyms :

Calculated chemistry of [ 119-68-6 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	42.71
TPSA :	49.33 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.57
Log Po/w (XLOGP3) :	2.03
Log Po/w (WLOGP) :	1.24
Log Po/w (MLOGP) :	0.21
Log Po/w (SILICOS-IT) :	0.89
Consensus Log Po/w :	1.19

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.85

Water Solubility

Log S (ESOL) :	-2.33
Solubility :	0.711 mg/ml ; 0.0047 mol/l
Class :	Soluble
Log S (Ali) :	-2.69
Solubility :	0.306 mg/ml ; 0.00202 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.19
Solubility :	0.972 mg/ml ; 0.00643 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 119-68-6 ]

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 [ 119-68-6 ]

* 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 [ 119-68-6 ]
Downstream synthetic route of [ 119-68-6 ]

[ 119-68-6 ] Synthesis Path-Upstream 1~5

1
[ 119-68-6 ]
[ 917-61-3 ]
[ 604-50-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With acetic acid; sodium hydroxide In water at 75℃; for 4 h;	Sodium cyanate (28mmol) in water (25mL) was added to a solution of N-methyl anthranilic acid (20mmol) and acetic acid (0.2mL) in water (50mL) with stirring. When the temperature of the reaction mixture reached 40°C, NaOH was added in portions till the reaction temperature reach to 75°C. Stirring was continued without cooling for 4h, after which the crystals were filtered off and dissolved in boiling water (50mL). The solution was acidified with 50percent H₂SO₄ to pH 1–2. The precipitated crystals were filtered off, washed with water and recrystallized from 50percent acetic acid to give compound 2 (2.92g, 84percent); m p 278°C [24].
77%	Stage #1: With acetic acid In water at 50℃; for 1 h; Stage #2: at 50 - 80℃;	Sodium cyanate (30.15 g, 0.46 mol) was added to a slurry of N- methylanthranilic acid (50.0 g, 0.33 mol) in water (1 .75 L) and acetic acid (3.3 mL). The reaction mixture was heated to 50 °C for 1 h. The solution was slowly basified by the addition of sodium hydroxide (exothermic). The resulting solution was heated to 80 °C and stirred overnight. The reaction mixture was cooled to 0 ^°C and the resultant precipitate collected by filtration. The solid was dissolved in boiling water (200 mL) and acidified with cone, sulfuric acid to pH 2. The slurry was cooled to room temperature and filtered. The solid was dried in a vacuum oven to give 1 -methylquinazoline-2,4(1 H,3H)-dione (53 g, 0.30 mol, 77percent).¹ H NMR (300MHz, DMSO-d₆) δ = 1 1 .54 (br. s., 1 H), 8.00 (d, J = 7.7 Hz, 1 H), 7.77 (t, J = 7.9 Hz, 1 H), 7.43 (d, J = 8.6 Hz, 1 H), 7.28 (t, J = 7.5 Hz, 1 H), 3.33 (s, 3H)
69%	With acetic acid; sodium hydroxide In water at 40 - 75℃; for 4 h;	2-(Methylamino)benzoic acid (4.50 g, 0.0300 mol) and acetic acid (0.3 mL) were dissolved in water (158 mL), a solution of sodium isocyanate (2.76 g, 42.0 mmol) in water (54 mL) was added slowly at room temperature. The reaction mixture was heated to 40°C and added with sodium hydroxide (34.8 g, 0.870 mol). The temperature was raised to 75°C and the reaction solution was stirred for 4 hours, cooled to room temperature, filtered and the filter cake was dissolved in boiling water (10 mL). The system was adjusted to pH 1-2 with 50percent sulfuric acid solution (15 mL), filtered and the filter cake was washed with a small amount of water (3 mL) and dried under reduced pressure to give 1-methylquinazoline-2,4-dione (3.64 g, as a yellow solid) with a yield of 69percent. ¹H NMR: (400 MHz, DMSO-d₆) δ 11.55(s, 1H), 8.00(d, J = 8.0 Hz, 1H), 7.78(t, J = 8.0 Hz, 1H), 7.42(d, J = 8.0 Hz, 1H), 7.28(t, J = 8.0 Hz, 1H), 3.44(s, 3H). MS-ESI calcd. [M + H]⁺ 177, found 177.

Reference： [1] Chemistry of Heterocyclic Compounds, 2009, vol. 45, # 12, p. 1508 - 1514
[2] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2013, vol. 110, p. 324 - 332
[3] Patent: WO2016/92326, 2016, A1, . Location in patent: Page/Page column 97; 113
[4] Patent: EP3299371, 2018, A1, . Location in patent: Paragraph 0525; 0526
[5] Letters in Drug Design and Discovery, 2014, vol. 11, # 6, p. 712 - 720

2
[ 119-68-6 ]
[ 57-13-6 ]
[ 604-50-2 ]

Yield	Reaction Conditions	Operation in experiment
64.3%	at 150℃; for 5 h;	Urea (460 mmol) was heated to melt, then 2-methylaminobenzoic acid (46 mmol) was added. The mixture was stirred for 5 h at 150 °C and then cooled to below 100 °C. Water (70 mL) was added to quench the reaction. The precipitated was collected and recrystallized in a mixed solution of acetone (10 mL) and water (100 mL) to afford compound 1 as a white powder (5.25 g, 64.3percent); mp 278-279 °C; ¹H NMR (DMSO-d₆) δ (ppm): 3.43 (s, 3H), 7.26 (t, J = 12 Hz, 1H), 7.41 (d, J = 12 Hz, 1H), 7.75 (t, J = 15 Hz, 1H), 7.98 (d, J = 6 Hz, 1H), 11.54 (s, 1H). ESI-MS (m/z): 177 (M+H)⁺.

Reference： [1] Chemistry Letters, 2005, vol. 34, # 10, p. 1438 - 1439
[2] Medicinal Chemistry Research, 2014, vol. 23, # 5, p. 2169 - 2177
[3] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 13, p. 3405 - 3413
[4] Yakugaku Zasshi, 1916, # 417, p. 17[5] Chem.Abstr., 1917, vol. 11, p. 578
[6] European Journal of Medicinal Chemistry, 2018, vol. 152, p. 560 - 569

3
[ 590-28-3 ]
[ 119-68-6 ]
[ 604-50-2 ]

Reference： [1] Chemistry Letters, 2005, vol. 34, # 10, p. 1438 - 1439
[2] Chemistry of Heterocyclic Compounds, 1996, vol. 32, # 6, p. 708 - 711
[3] Yakugaku Zasshi, 1916, # 417, p. 17[4] Chem.Abstr., 1917, vol. 11, p. 578

4
[ 64-17-5 ]
[ 119-68-6 ]
[ 35472-56-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	for 20 h; Inert atmosphere; Reflux	Concentrated sulfuric acid (2 mL, 37 mmol, 98percent) was added to a stirred solution of 2-(methylamino)-benzoic acid 7 (1.1 g, 7.5 mmol) in anhydrous ethanol (16.5 mL). The solution was refluxed for 20 hours, or until the reaction was complete. The solvent was removed under reduced pressure and the residue was re-dissolved in water (20 mL) and neutralised with sodium hydroxide (5 M). The aqueous phase was extracted with chloroform (3 x 20 mL), the organic layers were combined, washed with brine (40 mL), dried over anhydrous magnesium sulfate and the solvent evaporated to yield a brown oil 8 in quantitative yield (1.3 g, 7.5 mmol, 100percent). Rf 0.40 (1/10 v/v ethyl acetate/hexane); IR (ZnSe cell, oil) vmax: 3378 (w, aromatic R2NH), 2981, 2906 (w, C-H), 1677 (s, C=O), 1579, 1517 (m, aromatic C=C), 1233 (s, aromatic R2NH, ester C-O), 1125, 1085 (m, aromatic C=C) cm-1; 1H NMR (300 MHz, d6-DMSO): δ 7.79 (1H, dd, 3J6-5 = 8.1 Hz, 4J6-4 = 1.4 Hz, 6-CH), 7.56 (1H, br, d, 3JNH-10 = 4.2 Hz, NH) 7.40 (1H, ddd, 3J5-6 ~ 3J5-4 = 7.8 Hz, 4J5-3=1.2 Hz, 5-CH), 6.71 (1H, d, 3J3-4 = 8.4 Hz, 3-CH), 6.57 (1H, dd, 3J4-3 ~ 3J4-5 = 7.8 Hz, 4-CH), 4.25 (2H, q, 3J8-9 = 7.02 Hz, 8-CH2-), 2.91 (3H, d, 3J10-NH = 5.1 Hz, 10-CH3), 1.30 (3H, t, 3J9-8 = 7.2 Hz, 9-CH3) ppm; 13C NMR (125 MHz, CDCl3): δ 168.0 (7-C=O), 151.4 (2-C), 133.8 (4-CH), 130.9 (6-CH), 113.6 (5-CH), 110.0 (3-CH), 109.5 (1-C), 59.5 (8-CH2-), 28.8 (10-CH3), 13.7 (9-CH3) ppm; LRMS (+ ESI) m/z: 180 ([M + H]+, 100percent), 162 ([M – C3H5O2 + MeOH + Na + H]+ 56percent), 134 ([M - OCH2CH3]+, 47percent), 130 ([M - (CO2CH2CH3) + Na + H]+, 48percent)

Reference： [1] European Journal of Medicinal Chemistry, 2015, vol. 95, p. 29 - 34
[2] Chemische Berichte, 1901, vol. 34, p. 1645
[3] Chem. Zentralbl., 1906, vol. 77, # II, p. 1007
[4] Chemische Berichte, 1920, vol. 53, p. 2354
[5] Archiv der Pharmazie (Weinheim, Germany), 1925, p. 494
[6] Organic and Biomolecular Chemistry, 2011, vol. 9, # 20, p. 7113 - 7125

5
[ 119-68-6 ]
[ 29055-08-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With lithium aluminium tetrahydride In tetrahydrofuran for 1 h; Heating / reflux	a) Preparation of 2-(N-methylamino)-benzylalcohol [00260] To a suspension of lithium aluminum hydride (0.76 g, 0.02 mol) in dry tetrahydrofuran (40 ml) was added a solution of N-methylanthranilic acid(a) (1.51 g, 0.01 mol) in dry tetrahydrofuran under Ar atmosphere. After refluxing for 1 h, the reaction was quenched by adding ice water (50 ml). The mixture was filtered on a celite pad and thoroughly washed with dichloromethane (50 ml). The organic layer was separated and the water layer was extracted with dichloromethane (50 ml). The combined organic layer was washed with brine (30 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting yellowish oil was purified on a column of silica gel (wakogel. C-200 50 g, eluent n-hexane: ethyl acetate=2:1) to give the title compound(b) as colorless oil (1.18 g, 86percent). ¹H-NMR (270 MHz, CDCl₃): δ 2.87 (3H, s), 3.00-3.10 (1H, br.s), 4.64 (2H, s), 6.65-6.69 (2H, m), 7.05 (1H, d, J=7.2), 7.23-7.29 (1H, m)

Reference： [1] Patent: US6812238, 2004, B1, . Location in patent: Page/Page column 21; 31-32
[2] Organic Letters, 2016, vol. 18, # 21, p. 5572 - 5575

[ 119-68-6 ] Synthesis Path-Downstream 1~34

1
[ 67-56-1 ]
[ 119-68-6 ]
[ 85-91-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With hydrogenchloride
44%	With hydrogenchloride; thionyl chloride for 7h; Heating;
30%	With sulfuric acid Reflux;	17 Synthesis of 118-1 A solution of 118-0 (3.00 g, 20.0 mmol) and con.H2S04 (1 mL) in MeOH (20 mL) was heated at reflux overnight. The solvent was removed in vacuo. The residue was dissolved with EtOAc (50 mL). The resulting solution was washed with sat.NaHCOs (30 mL x 3) and brine (30 mL x 3). The organic layer was dried over anhydrous Na2S04 and then concentrated to give 118- 1 (1.0 g, 30 %) as a yellow solid

	With hydrogenchloride
	With sulfuric acid
	With hydrogenchloride
	With sulfuric acid Reflux;
	Stage #1: methanol; N-Methylanthranilic acid With sulfuric acid for 2h; Reflux; Stage #2: With ammonium hydroxide In water

Reference： [1]Jackman,L.M.; Trewella,J.C.; Haddon,R.C. [Journal of the American Chemical Society, 1980, vol. 102, p. 2519]
[2]Kavalek, Jaromir; Kralikova, Ulrika; Machacek, Vladimir; Sedlak, Milos; Sterba, Vojeslav [Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 1, p. 202 - 222]
[3]Current Patent Assignee: ALKERMES PLC - WO2015/200619, 2015, A1 Location in patent: Paragraph 0332
[4]Schroeter; Eisleb [Justus Liebigs Annalen der Chemie, 1909, vol. 367, p. 158] Schultz,G.; Flachslaender [Chemisches Zentralblatt, 1902, vol. 73, # II, p. 448] Current Patent Assignee: Schimmel & Co. - DE122568, 1800, C
[5]Current Patent Assignee: Schimmel & Co. - DE122568, 1800, C
[6]Keller; Schulze [Archiv der Pharmazie, 1925, p. 494] Current Patent Assignee: Schimmel & Co. - DE122568, 1800, C
[7]Location in patent: experimental part Jiang, Qian-Qian; Darhkijav, Burenkhangai; Liu, Hao; Wang, Fang; Li, Zhao; Jiang, Yun-Bao [Chemistry - An Asian Journal, 2010, vol. 5, # 3, p. 543 - 549]
[8]Location in patent: experimental part Cheng, Yih-Dih; Hwang, Tsong-Long; Wang, Han-Hsiang; Pan, Tai-Long; Wu, Chin-Chung; Chang, Wen-Yi; Liu, Yi-Ting; Chu, Tzu-Chi; Hsieh, Pei-Wen [Organic and Biomolecular Chemistry, 2011, vol. 9, # 20, p. 7113 - 7125]

2
[ 64-17-5 ]
[ 119-68-6 ]
[ 35472-56-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sulfuric acid; for 20h;Inert atmosphere; Reflux;	Concentrated sulfuric acid (2 mL, 37 mmol, 98%) was added to a stirred solution of 2-(methylamino)-benzoic acid 7 (1.1 g, 7.5 mmol) in anhydrous ethanol (16.5 mL). The solution was refluxed for 20 hours, or until the reaction was complete. The solvent was removed under reduced pressure and the residue was re-dissolved in water (20 mL) and neutralised with sodium hydroxide (5 M). The aqueous phase was extracted with chloroform (3 x 20 mL), the organic layers were combined, washed with brine (40 mL), dried over anhydrous magnesium sulfate and the solvent evaporated to yield a brown oil 8 in quantitative yield (1.3 g, 7.5 mmol, 100%). Rf 0.40 (1/10 v/v ethyl acetate/hexane); IR (ZnSe cell, oil) vmax: 3378 (w, aromatic R2NH), 2981, 2906 (w, C-H), 1677 (s, C=O), 1579, 1517 (m, aromatic C=C), 1233 (s, aromatic R2NH, ester C-O), 1125, 1085 (m, aromatic C=C) cm-1; 1H NMR (300 MHz, d6-DMSO): delta 7.79 (1H, dd, 3J6-5 = 8.1 Hz, 4J6-4 = 1.4 Hz, 6-CH), 7.56 (1H, br, d, 3JNH-10 = 4.2 Hz, NH) 7.40 (1H, ddd, 3J5-6 ~ 3J5-4 = 7.8 Hz, 4J5-3=1.2 Hz, 5-CH), 6.71 (1H, d, 3J3-4 = 8.4 Hz, 3-CH), 6.57 (1H, dd, 3J4-3 ~ 3J4-5 = 7.8 Hz, 4-CH), 4.25 (2H, q, 3J8-9 = 7.02 Hz, 8-CH2-), 2.91 (3H, d, 3J10-NH = 5.1 Hz, 10-CH3), 1.30 (3H, t, 3J9-8 = 7.2 Hz, 9-CH3) ppm; 13C NMR (125 MHz, CDCl3): delta 168.0 (7-C=O), 151.4 (2-C), 133.8 (4-CH), 130.9 (6-CH), 113.6 (5-CH), 110.0 (3-CH), 109.5 (1-C), 59.5 (8-CH2-), 28.8 (10-CH3), 13.7 (9-CH3) ppm; LRMS (+ ESI) m/z: 180 ([M + H]+, 100%), 162 ([M - C3H5O2 + MeOH + Na + H]+ 56%), 134 ([M - OCH2CH3]+, 47%), 130 ([M - (CO2CH2CH3) + Na + H]+, 48%)

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 95,p. 29 - 34
[2]Chemische Berichte,1901,vol. 34,p. 1645
[3]Chemische Berichte,1920,vol. 53,p. 2354
[4]Archiv der Pharmazie,1925,p. 494
[5]Organic and Biomolecular Chemistry,2011,vol. 9,p. 7113 - 7125

3
[ 590-28-3 ]
[ 119-68-6 ]
[ 604-50-2 ]

Reference： [1]Chemistry Letters,2005,vol. 34,p. 1438 - 1439
[2]Chemistry of Heterocyclic Compounds,1996,vol. 32,p. 708 - 711
[3]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1916,p. 17
Chem.Abstr.,1917,vol. 11,p. 578

4
[ 119-68-6 ]
[ 3260-63-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; chloroacetic acid Erhitzen des Reaktionsprodukts mit Acetanhydrid und Natriumacetat;

Reference： [1]Ettinger; Friedlaender [Chemische Berichte, 1912, vol. 45, p. 2078]

5
[ 119-68-6 ]
[ 22721-16-0 ]

Yield	Reaction Conditions	Operation in experiment
	With chloroform; bromine
	With bromine; acetic acid

Reference： [1]Heilbron; Holt; Kitchen [Journal of the Chemical Society, 1928, p. 936,939]
[2]Heilbron; Holt; Kitchen [Journal of the Chemical Society, 1928, p. 936,939]

6
[ 124341-38-4 ]
[ 119-68-6 ]
[ 766491-67-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; tin

Reference： [1]Keller [Archiv der Pharmazie, 1908, vol. 246, p. 15,21]

7
[ 64-17-5 ]
[ 118-92-3 ]
furan-2,3,5(4H)-trione pyridine (1:1) [ No CAS ]
[ 74-88-4 ]
[ 610-16-2 ]
[ 119-68-6 ]

Reference： [1]Chemische Berichte,1904,vol. 37,p. 406

8
[ 119-68-6 ]
[ 57-13-6 ]
[ 604-50-2 ]

Yield	Reaction Conditions	Operation in experiment
64.3%	at 150℃; for 5h;	Urea (460 mmol) was heated to melt, then 2-methylaminobenzoic acid (46 mmol) was added. The mixture was stirred for 5 h at 150 C and then cooled to below 100 C. Water (70 mL) was added to quench the reaction. The precipitated was collected and recrystallized in a mixed solution of acetone (10 mL) and water (100 mL) to afford compound 1 as a white powder (5.25 g, 64.3%); mp 278-279 C; 1H NMR (DMSO-d6) delta (ppm): 3.43 (s, 3H), 7.26 (t, J = 12 Hz, 1H), 7.41 (d, J = 12 Hz, 1H), 7.75 (t, J = 15 Hz, 1H), 7.98 (d, J = 6 Hz, 1H), 11.54 (s, 1H). ESI-MS (m/z): 177 (M+H)+.

Reference： [1]Chemistry Letters,2005,vol. 34,p. 1438 - 1439
[2]Medicinal Chemistry Research,2014,vol. 23,p. 2169 - 2177
[3]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 3405 - 3413
[4]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1916,p. 17
Chem.Abstr.,1917,vol. 11,p. 578
[5]European Journal of Medicinal Chemistry,2018,vol. 152,p. 560 - 569

9
[ 119-68-6 ]
[ 1566-32-1 ]
[ 89988-66-9 ]

Yield	Reaction Conditions	Operation in experiment
74%	at 180℃; for 1.5h;

Reference： [1]Abdel-Hady, Sayed A. L.; Badawy, Mohamed A.; Ibrahim, Yehia A.; Pfleiderer, Wolfgang [Chemische Berichte, 1984, vol. 117, # 3, p. 1077 - 1082]

10
[ 119-68-6 ]
[ 1566-32-1 ]
[ 89988-67-0 ]

Yield	Reaction Conditions	Operation in experiment
78%	at 180℃; for 1.5h;

Reference： [1]Abdel-Hady, Sayed A. L.; Badawy, Mohamed A.; Ibrahim, Yehia A.; Pfleiderer, Wolfgang [Chemische Berichte, 1984, vol. 117, # 3, p. 1077 - 1082]

11
[ 119-68-6 ]
[ 90002-02-1 ]
[ 107733-46-0 ]

Yield	Reaction Conditions	Operation in experiment
	Yield given;

Reference： [1]Rahman [Bulletin des Societes Chimiques Belges, 1986, vol. 95, # 2, p. 141 - 142]

12
[ 119-68-6 ]
[ 1121-57-9 ]
[ 104-87-0 ]
[ 64-04-0 ]
1-Methyl-4-phenethyl-3-p-tolyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	With acetyl chloride In methanol at 55℃; for 6h;

Reference： [1]Keating, Thomas A.; Armstrong, Robert W. [Journal of Organic Chemistry, 1996, vol. 61, # 25, p. 8935 - 8939]

13
[ 924-73-2 ]
[ 119-68-6 ]
[ 1121-57-9 ]
[ 78-84-2 ]
3-(3-Isopropyl-1-methyl-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-propionic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With hydrogenchloride In methanol; diethyl ether; toluene at 100℃; for 6h;

Reference： [1]Keating, Thomas A.; Armstrong, Robert W. [Journal of Organic Chemistry, 1996, vol. 61, # 25, p. 8935 - 8939]

14
[ 119-68-6 ]
[ 150374-99-5 ]
[ 188115-02-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,1996,vol. 4,p. 2115 - 2134

15
[ 119-68-6 ]
[ 14152-97-7 ]
1-methyl-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-quinazoline-2,4(1H,3H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With silver trifluoroacetate; triethylamine In acetonitrile at 50℃; for 5h;

Reference： [1]Gama, Yasuo; Shibuya, Isao; Shimizu, Masao [Synthetic Communications, 1999, vol. 29, # 9, p. 1493 - 1501]

16
[ 7647-01-0 ]
[ 124341-38-4 ]
[ 119-68-6 ]
[ 766491-67-2 ]

Reference： [1]Keller [Archiv der Pharmazie, 1908, vol. 246, p. 15,21]

17
[ 118-92-3 ]
[ 616-38-6 ]
[ 610-16-2 ]
[ 119-68-6 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 7374 - 7378

18
[ 119-68-6 ]
[ 145489-90-3 ]
10-bromo-14-methyl-8,13,13b,14-tetrahydro-7<i>H</i>-indolo[2',3':3,4]pyrido[2,1-<i>b</i>]quinazolin-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate In toluene for 1h; Heating;

Reference： [1]Baruah, Bipul; Dasu, Kavitha; Vaitilingam, Balasubramanian; Mamnoor, Premkumar; Venkata, Prasanthi Penubaka; Rajagopal, Sriram; Yeleswarapu, Koteswar Rao [Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 9, p. 1991 - 1994]

19
[ 118-92-3 ]
[ 141814-27-9 ]
[ 610-16-2 ]
[ 119-68-6 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 2476 - 2485

20
[ 119-68-6 ]
[ 57513-54-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N,N'-dicyclohexylcarbodiimide / tetrahydrofuran / 3 - 5 °C 2: 1.5 g / NaH / tetrahydrofuran / 2.5 h / 20 °C

Reference： [1]Zikou, Lamprini; Athanasellis, Giorgos; Detsi, Anastasia; Zografos, Alexandros; Mitsos, Christos; Igglessi-Markopoulou, Olga [Bulletin of the Chemical Society of Japan, 2004, vol. 77, # 8, p. 1505 - 1508]

21
[ 119-68-6 ]
[ 766491-67-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sulfuric acid; sodium nitrite / 80 °C 2: tin; hydrochloric acid

Reference： [1]Keller [Archiv der Pharmazie, 1908, vol. 246, p. 15,21]

22
[ 119-68-6 ]
[ 29055-08-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h;Heating / reflux;	a) Preparation of 2-(N-methylamino)-benzylalcohol [00260] To a suspension of lithium aluminum hydride (0.76 g, 0.02 mol) in dry tetrahydrofuran (40 ml) was added a solution of N-methylanthranilic acid(a) (1.51 g, 0.01 mol) in dry tetrahydrofuran under Ar atmosphere. After refluxing for 1 h, the reaction was quenched by adding ice water (50 ml). The mixture was filtered on a celite pad and thoroughly washed with dichloromethane (50 ml). The organic layer was separated and the water layer was extracted with dichloromethane (50 ml). The combined organic layer was washed with brine (30 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting yellowish oil was purified on a column of silica gel (wakogel. C-200 50 g, eluent n-hexane: ethyl acetate=2:1) to give the title compound(b) as colorless oil (1.18 g, 86percent). 1H-NMR (270 MHz, CDCl3): delta 2.87 (3H, s), 3.00-3.10 (1H, br.s), 4.64 (2H, s), 6.65-6.69 (2H, m), 7.05 (1H, d, J=7.2), 7.23-7.29 (1H, m)

Reference： [1]Patent: US6812238,2004,B1 .Location in patent: Page/Page column 21; 31-32
[2]Organic Letters,2016,vol. 18,p. 5572 - 5575

23
[ 85-91-6 ]
[ 119-68-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: Methyl N-methylanthranilate With sodium hydroxide In methanol; water at 0 - 50℃; for 6h; Stage #2: With hydrogenchloride In water	9 Preparation 9: N-Methyl anthranilic acid To a solution of methyl-N-methyl anthranilate (20 g, 121 mmol) in methanol (100 mL), placed in a 250 mL single neck round bottomed flask, was added a solution of NaOH (9.69 g, 242 mmol) in 25 mL of water at 0-10 °C. The reaction mixture was heated to 50 °C for 6 h and then cooled to room temparature. Methanol was removed completely from the reaction mixture and water (100 mL) was added to it. The mixture was then washed with ether (3 x 50 mL) and the aqueous layer was acidified (pH-5-6) with ice cold 2 N HCI. The solid that separated was filtered, washed with water (2 x 50 mL) and dried under vacuum to afford the title compound 17.0 g (93 %) as a white color solid.
92%	With sodium hydroxide In diethyl ether at 20℃; for 4h;	To a 100 round bottom flask were added methyl 2-aminobenzoate (1.51 g, 10 mmol),acetic acid (2.40 g, 40 mmol), aqueous formaldehyde (35%, 0.92 g, ca. 40 mmol),zinc dust (1.31 g, 20 mmol) and 30 mL of 1,4-dioxane. The mixture was heated at60 °C for 5 h. The reaction mixture was then cooled to room temperature and thereaction was quenched with excess amount of aqueous ammonia. The reactionmixture was extracted with dichloromethane (50 mL × 3). The organic layer wascombined and dried over MgSO4. The solvent was removed and the crude productwas purified by column chromatography to give 1.32 g methyl2-(N-methylamino)benzoate (80%).To a solution of 2-(N-methylamino)benzoate (0.76 g, 5 mmol) in 20 mL of diethylether was added excess amount of NaOH (20 mmol). The reaction mixture was stirredat room temperature for 4 h, and the aqueous phase was separated. The pH value ofthe aqueous layer was adjusted to 2.0 by addition of diluted hydrochloric acid, andwas extracted 3 times with ethyl acetate (100 mL × 3). The organic phase was driedwith MgSO4, and was concentrated in vacuo. The crude product was purified bycolumn chromatography to give the 2i. Column chromatography (petroleum ether:ethyl acetate= 15:1) gave 2i as a white powder: 1.39 g, 92%, m. p. =170-172 °C. 1HNMR (400 MHz, CDCl3) δ =7.98 (dd, J = 8.0, 1.5 Hz, 1H), 7.44-7.40 (m, 1H), 6.68 (d,J = 8.5 Hz, 1H), 6.62 (t, J = 7.5 Hz, 1H), 2.93 (s, 3H). 13C NMR (100 MHz, CDCl3)δ= 174.0, 152.7, 135.7, 132.6, 114.6, 110.9, 108.6, 29.6. NMR data were in agreementwith reported results.5
90%	With sodium hydroxide In methanol; water at 60℃; for 1h;

	Multi-step reaction with 2 steps 1.1: trichlorophosphate / tetrahydrofuran / 1.5 h / 60 °C / Inert atmosphere 1.2: 41 h / 75 °C / Inert atmosphere 2.1: potassium hydroxide / isopropyl alcohol; toluene / 2 h / Reflux 2.2: pH 5
	Multi-step reaction with 2 steps 1.1: trichlorophosphate / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere 1.2: 96 h / 75 °C / Inert atmosphere 2.1: potassium hydroxide / isopropyl alcohol; toluene / 2 h / Reflux 2.2: pH 5
	Multi-step reaction with 2 steps 1.1: trichlorophosphate / tetrahydrofuran / 96 h 2.1: potassium hydroxide / isopropyl alcohol; toluene / 2 h / Reflux 2.2: pH 5

Reference： [1]Current Patent Assignee: DR REDDY&apos;S LABORATORIES LIMITED - WO2005/40163, 2005, A1 Location in patent: Page/Page column 61
[2]Li, Ting-Ting; Liu, Gong-Qing; Wang, Yu-Mei; Cui, Bin; Sun, Hui; Li, Yue-Ming [Tetrahedron, 2015, vol. 71, # 38, p. 7003 - 7009]
[3]Ji, Qing-Gang; Yang, Dan; Deng, Qiao; Ge, Zhi-Qiang; Yuan, Lv-Jiang [Medicinal Chemistry Research, 2014, vol. 23, # 5, p. 2169 - 2177]
[4]Wehle, Sarah; Espargaró, Alba; Sabaté, Raimon; Decker, Michael [Tetrahedron, 2016, vol. 72, # 20, p. 2535 - 2543]
[5]Wehle, Sarah; Espargaró, Alba; Sabaté, Raimon; Decker, Michael [Tetrahedron, 2016, vol. 72, # 20, p. 2535 - 2543]
[6]Wehle, Sarah; Espargaró, Alba; Sabaté, Raimon; Decker, Michael [Tetrahedron, 2016, vol. 72, # 20, p. 2535 - 2543]

24
[ 119-68-6 ]
[ 665-66-7 ]
N-adamantan-1-yl-2-(methylamino)-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%		N,N-Carbonyldiimidazole (0.33 g, 2.035 mmol) was added to a solution of N-methylanthranilic acid (0.28 g, 1.85 mmol) in tetrahydrofuran (10 mL). The resulting solution was protected from light and stirred at room temperature for 24 h. A solution of <strong>[665-66-7]amantadine hydrochloride</strong> (0.280 g, 1.85 mmol) in tetrahydrofuran (10 mL) and triethylamine (0.615 g) was added slowly. The resulting solution was protected from light and stirred for 48 h at room temperature. The reaction mixture was added to water and extracted with DCM (3 × 100 mL). The organic phase was collected, dried (MgSO4) and the solvent was removed in vacuo rendering the product as a yellow oil. The yellow oil was added to ethyl acetate and a precipitate formed upon standing. The precipitate was filtered and washed with cold ethyl acetate (2 × 15 mL), yielding the product as a light-yellow amorphous solid (0.388 g, 1.35 mmol, 73%).Physical data: C18H24N2O; mp: 213 C; 1H NMR (200 MHz, CDCl3) deltaH: 8.01-7.97 (dd, J = 6.5 and 2.2 Hz,1H), 7.28 (m, 2H), 6.56-6.62 (m, 3H), 2.86 (s, 3H), 2.00 (s, 3H), 1.86 (d, 6H), 1.62-1.44 (m, 6H); 13C NMR (50 MHz, CDCl3) deltaC: 175.01, 151.75, 132.74, 132.49, 117.54, 113.96, 110.05, 51.09, 40.98, 35.80, 29.74, 29.12; MS (EI, 70 eV) m/z: 284 (M+). HREI-MS: Calcd for C18H24N2O (MH+); 284.18889, found 284.18864. IR (ATR) numax: 3341, 2911, 2853, 1609, 1503, 1365, 754.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 3935 - 3944
[2]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 8952 - 8958

25
[ 119-68-6 ]
[ 917-61-3 ]
[ 604-50-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With acetic acid; sodium hydroxide; In water; at 75℃; for 4h;	Sodium cyanate (28mmol) in water (25mL) was added to a solution of N-methyl anthranilic acid (20mmol) and acetic acid (0.2mL) in water (50mL) with stirring. When the temperature of the reaction mixture reached 40C, NaOH was added in portions till the reaction temperature reach to 75C. Stirring was continued without cooling for 4h, after which the crystals were filtered off and dissolved in boiling water (50mL). The solution was acidified with 50% H2SO4 to pH 1-2. The precipitated crystals were filtered off, washed with water and recrystallized from 50% acetic acid to give compound 2 (2.92g, 84%); m p 278C [24].
77%		Sodium cyanate (30.15 g, 0.46 mol) was added to a slurry of N- methylanthranilic acid (50.0 g, 0.33 mol) in water (1 .75 L) and acetic acid (3.3 mL). The reaction mixture was heated to 50 C for 1 h. The solution was slowly basified by the addition of sodium hydroxide (exothermic). The resulting solution was heated to 80 C and stirred overnight. The reaction mixture was cooled to 0 C and the resultant precipitate collected by filtration. The solid was dissolved in boiling water (200 mL) and acidified with cone, sulfuric acid to pH 2. The slurry was cooled to room temperature and filtered. The solid was dried in a vacuum oven to give 1 -methylquinazoline-2,4(1 H,3H)-dione (53 g, 0.30 mol, 77%).1 H NMR (300MHz, DMSO-d6) delta = 1 1 .54 (br. s., 1 H), 8.00 (d, J = 7.7 Hz, 1 H), 7.77 (t, J = 7.9 Hz, 1 H), 7.43 (d, J = 8.6 Hz, 1 H), 7.28 (t, J = 7.5 Hz, 1 H), 3.33 (s, 3H)
69%	With acetic acid; sodium hydroxide; In water; at 40 - 75℃; for 4h;	2-(Methylamino)benzoic acid (4.50 g, 0.0300 mol) and acetic acid (0.3 mL) were dissolved in water (158 mL), a solution of sodium isocyanate (2.76 g, 42.0 mmol) in water (54 mL) was added slowly at room temperature. The reaction mixture was heated to 40C and added with sodium hydroxide (34.8 g, 0.870 mol). The temperature was raised to 75C and the reaction solution was stirred for 4 hours, cooled to room temperature, filtered and the filter cake was dissolved in boiling water (10 mL). The system was adjusted to pH 1-2 with 50% sulfuric acid solution (15 mL), filtered and the filter cake was washed with a small amount of water (3 mL) and dried under reduced pressure to give 1-methylquinazoline-2,4-dione (3.64 g, as a yellow solid) with a yield of 69%. 1H NMR: (400 MHz, DMSO-d6) delta 11.55(s, 1H), 8.00(d, J = 8.0 Hz, 1H), 7.78(t, J = 8.0 Hz, 1H), 7.42(d, J = 8.0 Hz, 1H), 7.28(t, J = 8.0 Hz, 1H), 3.44(s, 3H). MS-ESI calcd. [M + H]+ 177, found 177.

Reference： [1]Chemistry of Heterocyclic Compounds,2009,vol. 45,p. 1508 - 1514
[2]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2013,vol. 110,p. 324 - 332
[3]Patent: WO2016/92326,2016,A1 .Location in patent: Page/Page column 97; 113
[4]Journal of Medicinal Chemistry,2018,vol. 61,p. 10767 - 10792
[5]Patent: EP3299371,2018,A1 .Location in patent: Paragraph 0525; 0526
[6]Letters in drug design and discovery,2014,vol. 11,p. 712 - 720

26
[ 119-68-6 ]
[ 7505-81-9 ]

Yield	Reaction Conditions	Operation in experiment
15%	Stage #1: N-Methylanthranilic acid In dichloromethane; N,N-dimethyl-formamide for 4.5h; Inert atmosphere; Reflux; Cooling with ice; Stage #2: With ammonia In dichloromethane; water; N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 3 h / 20 °C / Inert atmosphere 2: ammonium hydroxide / water; dichloromethane / 1 h / 20 °C / Inert atmosphere

Reference： [1]Paleta, Oldrich; Dolensky, Bohumil; Palecek, Jiri; Kvicala, Jaroslav [European Journal of Organic Chemistry, 2013, # 7, p. 1262 - 1270]
[2]Chen, Zhe-Sheng; Li, Dahong; Qiu, Yangyi; Wu, Liang; Xu, Jinyi; Xu, Shengtao; Yang, Dong-Hua; Yao, Hong; Zhou, Manzhen [Journal of Medicinal Chemistry, 2021, vol. 64, # 23, p. 17346 - 17365]

27
[ 119-68-6 ]
[ 18807-71-1 ]
benzyl 2-(2-(methylamino)benzamido)ethylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20℃;	First, 0.164 g (1.08 mmol) of 2-(methylamino)benzoic acid wassolved at 0 C in 20 ml of DMF and treated with 0.25 g of benzyl2-aminoethylcarbamateHCl (1.08 mmol), 0.38 ml (2.16 mmol) ofDIPEA, and 0.279 g (1.08 mmol) of benzotriazolyl-1-oxytris(dimethylamino)phosphonium hexafluorophosphate (BOP).The mixture was stirred for 15 min at 0 C and at room temperatureovernight. The solvent was removed in vacuo, and the intermediatebenzyl 2-(2-(methylamino)benzamido) ethylcarbamatewas purified by preparative reversed phase HPLC. The solventwas evaporated in vacuo, and the remaining oil was treated with3 ml of 32% HBr in acetic acid for 1 h. The product was precipitatedby the addition of diethyl ether, filtered, and purified bypreparative HPLC (brownish oil; HPLC: 14.5 min; MS: calc.193.1, found 194.1 (M+H)+; NMR: 13C NMR (101 MHz, DMSOd6):d [ppm] = 170.23, 150.59, 133.13, 128.92, 114.91, 114.36,111.10, 39.17, 37.31, 29.74).

Reference： [1]Analytical Biochemistry,2013,vol. 442,p. 223 - 230

28
[ 3382-18-1 ]
[ 119-68-6 ]
2,3-dimethoxy-13-methyl-5,6,13,13a-tetrahydro-8H-isoquinolino[1,2-b]quinazolin-8-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In toluene; at 90℃; for 20h;	General procedure: To a solution of imine (1 mmol) and acid (1.2 mmol) in dry toluene (10 mL) was added sequentially DIPEA (1.85 mmol) andthen T3P (1.5 mmol, 50% in THF). The resulting solution was heatedat 90C or 120C in a sealable tube for the specified time, before cooling to RT and pouring into satd aq NaHCO3 (20 mL). The aqueous layer was extracted with DCM (330 mL), concentrated in vacuo and purified by column chromatography.

Reference： [1]Tetrahedron,2014,vol. 70,p. 7172 - 7180

29
[ 119-68-6 ]
[ 32854-09-4 ]
C₂₄H₃₀N₄O₆S₂ [ No CAS ]

Reference： [1]Australian Journal of Chemistry,2015,vol. 68,p. 1829 - 1833

30
2-[2-(methylamino)benzoyl]-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]
[ 119-68-6 ]
[ 1196-38-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-[2-(methylamino)benzoyl]-3,4-dihydroisoquinolin-1(2H)-one With potassium hydroxide In isopropyl alcohol; toluene for 2h; Reflux; Stage #2: In water	3.3 Procedure and experimental data for stability testing General procedure: For stability tests compounds 2b and 4b (15 μmol) were dissolved in dry toluene (3.0 mL) and the additive (10.0 eq. HCl, 10.0 eq KOH or 10.0 eq water) was added. For the DABCO experiment, benz-DHED 4b was dissolved in toluene, 13.0 eq diazabicyclooctane (DABCO) and after 10 min of stirring 10.0 eq. HCl were added. The reaction mixture was heated for 2 ;h to 115 °C oil bath temperature. Removal of the solvent yielded the products which were directly measured in NMR and LCMS. Only for the additive KOH an extraction protocol (acidified water to pH 5 (10 mL), CH2Cl2 (3*10 mL)) was performed. Reaction products were analyzed by LCMS as fast and simple detection method and 1H-NMR spectroscopy.

Reference： [1]Wehle, Sarah; Espargaró, Alba; Sabaté, Raimon; Decker, Michael [Tetrahedron, 2016, vol. 72, # 20, p. 2535 - 2543]

31
[ 201230-82-2 ]
[ 109-73-9 ]
[ 100-61-8 ]
[ 1792-17-2 ]
[ 53693-74-6 ]
[ 119-68-6 ]
[ 53693-72-4 ]
[ 10328-92-4 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 4634 - 4637

32
[ 610-16-2 ]
[ 119-68-6 ]

Reference： [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 687 - 692
[2]Journal of Organic Chemistry,2020,vol. 85,p. 2672 - 2679

33
[ 24424-99-5 ]
[ 119-68-6 ]
[ 141871-02-5 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; triethylamine; In acetonitrile; at 20℃; for 2h;	General procedure: To a solution of anthranilic acid (0.5g, 3.64mmol) in acetonitrile (10mL) were added TEA (0.73g, 7.28mmol), Boc anhydride (0.95g, 4.37mmol), and DMAP (0.044g, 0.36mmol). The mixture was stirred at rt for 2.0 h. CMPI (1.1g, 4.36mmol) was added in one lot to the reaction mixture. The reaction mixture was stirred at rt for 10 min. 1N HCl (20mL) was added to the reaction and the mixture was extracted two times with EtOAc. The combined organic layers were washed with brine, dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting solid was crystallized in DCM and MeOH to afford 0.56g (95%) of 1H-benzo[d][1,3]oxazine-2,4-dione as an off white solid. 1H NMR (400MHz, DMSO) δ 7.14-7.16 (d, J=8Hz, 1H), 7.23-7.27 (t, J=16Hz,1H), 7.72-7.74 (t, J=8Hz, 1H), 7.90-7.92 (d, J=8Hz,1H), 11.72 (s, 1H). 13C NMR (100MHz, DMSO-d6) δ 110.6, 115.7, 123.9, 129.3, 137.3, 141.8, 147.5, 160.3. IR (thin film) 3461, 3173, 2937, 1984, 1753, 1604, 1486, 1358, 1258, 1138, 1009, 765, 673, 492. ES-MS (m/z): 161.8 (M+-H). MP (C): 236.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 6897 - 6899

34
[ 4693-02-1 ]
[ 119-68-6 ]
C₁₅H₁₃N₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In water; at 80℃; for 0.5h;	General procedure: A suspension of 1H-benzo[d][1,3]oxazine-2,4-dione 13a-i (1 equiv.), 2-aminobenzoic acid 14a-d (1 equiv.) and sodium hydroxide (1 equiv.) in water (10 mL/mmol) was heated at 80 C for 30 min until the evolution of carbon dioxide had ceased and a clear solution had formed. After cooling the reaction mixture, the obtained solution was diluted with water, and the crude product was precipitated by addition of glacial acetic acid, filtered and dried under vacuum. In cases of N-alkyl 1H-benzo[d][1,3]oxazine-2,4-diones where a gummy-like residue was formed, the crude product was extracted with ethyl acetate, the organic phase was washed with brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent left a glass-like residue which was used in next step without further purification.

Reference： [1]Molecules,2020,vol. 25

Same Skeleton Products

Related Products

Historical Records

Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
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. 119-68-6 ] {[proInfo.proName]}

Quality Control of [ 119-68-6 ]

Related Doc. of [ 119-68-6 ]

Product Details of [ 119-68-6 ]

Calculated chemistry of [ 119-68-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 119-68-6 ]

Application In Synthesis of [ 119-68-6 ]

[ 119-68-6 ] Synthesis Path-Upstream 1~5

[ 119-68-6 ] Synthesis Path-Downstream 1~34

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry