22246-83-9|8-Methoxy-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one| Ambeed

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Quality Control of [ 22246-83-9 ] Purity: 95% SDS Specification

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Product Details of [ 22246-83-9 ]

CAS No. :	22246-83-9
Formula :	C₁₁H₁₃NO₂
M.W :	191.23
SMILES Code :	O=C1CCCC2=CC=C(OC)C=C2N1
MDL No. :	MFCD00667666
InChI Key :	BKZDEMMOMTUSPL-UHFFFAOYSA-N
Pubchem ID :	676953

Safety of [ 22246-83-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 22246-83-9 ]

* 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 [ 22246-83-9 ]

[ 22246-83-9 ] Synthesis Path-Downstream 1~35

1
[ 22246-83-9 ]
[ 17422-43-4 ]

Yield	Reaction Conditions	Operation in experiment
89%		Reference Example 65 8-methoxy-2,3,4, 5-tetrahydro-1 H-1-benzazepine To a suspension of lithium aluminum hydride (725 mg, 19.1 mmol) in THF (15 mL) was added dropwise a solution of <strong>[22246-83-9]8-methoxy-1,3,4, 5-tetrahydro-2H-1-benzazepin-2-one</strong> (1.46 g, 7.63 mmol) in THF (20 mL) under ice-cooling, and the mixture was refluxed for 4 hr. The reaction mixture was treated by adding dropwise water (0.75 mL), 15% aqueous sodium hydroxide solution (0.75 mL) and water (2.25 mL). The precipitate was filtered and the obtained solid was washed with ethyl acetate. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (1.20 g, yield 89%) as an oil. 1H-NMR (CDCl3) δ: 1.55 - 1.69 (2H, m), 1.72 - 1.89 (2H, m), 2.64 - 2.78 (2H, m), 2.99 - 3.12 (2H, m), 3.75 (4H, s), 6.30 (1H, d, J = 2.6 Hz), 6.38 (1H, dd, J = 8.2, 2.5 Hz), 6.99 (1H, d, J = 8.1 Hz).
1.9 g	With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h;Reflux;	Example 3. 8-methoxy-2,3,4,5-tetrahydro-lH-benzo[b]azepine [00164] To a solution of 8-methoxy-4,5-dihydro-lH-benzo[b]azepin-2(3H)-one (2 g) in THF (100 mL), lithium aluminum hydride (0.79 g) was added, and the reaction heated to reflux. After stirring for 1 hour, the heat was removed. Water (6 mL) was added followed by NaOH (10%, 15 mL), the flocculated solids removed by filtration, and the eluent concentrated to provide the title compound (1.9 g) as a pale brown oil: IH NMR (DMSO-d6) δ 6.88 (d, IH); 6.37 (d, IH), 6.22 (dd, IH), 5.14 (s, IH), 3.62 (s, 3H), 2.90-2.85 (m, 2H), 2.57-2.53 (m, 2H), 1.67-1.59 (m, 2H), 1.52-1.45 (m, 2H).

References: [1]Patent: EP2298731,2011,A1 .Location in patent: Page/Page column 62-63.
[2]Journal of the Chemical Society. Perkin transactions I,1997,p. 3261 - 3273.
[3]Patent: WO2013/78244,2013,A1 .Location in patent: Paragraph 00163-00164.

2
[ 99833-87-1 ]
[ 22246-83-9 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 3261 - 3273.

3
[ 22246-83-9 ]
[ 145485-37-6 ]

Yield	Reaction Conditions	Operation in experiment
		Step B: 3-Iodo-8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one Prepared from 8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one by the procedure described in Example 31, Step B. 1 H NMR (200 MHz, CDCl3): 2.6-3.1 (m,4H), 3.88 (s,3H), 4.76 (t,6 Hz,1H), 6.68 (d,2 Hz,1H), 6.81 (dd;2,8 Hz;1H), 7.20 (d,2 Hz,1H). FAB-MS: calculated for C11 H12 INO2 317; found 318 (M+H,44%).

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2573 - 2578.
[2]Patent: US5206235,1993,A .

4
[ 20175-97-7 ]
[ 22246-83-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With polyphosphoric acid; at 70℃;	7-methoxy-3,4-dihydronaphthalen-1(2H)-one oxime (1.34 g, 7.0 mmol) was added to PPA (35.6 g, 200 mmol) and reaction mixture stirred overnight at 70 C. The reaction mixture was diluted with ice cold water and stirred for 30 min. It was then extracted with EtOAc and concentrated. Purification of crude product was performed on ISCO using pre-packed Silica gel column. Yield: 1.00 g (75%). 1H NMR (CDCl3) δ 7.54 (s, 1H), 7.11 (d, J=8.3 Hz, 1H), 6.69 (dd, J=8.3, 2.6 Hz, 1H), 6.53 (d, J=2.6 Hz, 1H), 3.79 (s, 3H), 2.74 (t, J=7.2 Hz, 2H), 2.36 (t, J=7.3 Hz, 2H), 2.19 (q, J=7.5 Hz, 2H). ESI-MS: m/z 192 [M+H]+.
6.56 g (73%)	With P2O5; In methanesulfonic acid;	Method B The title compound was prepared by the same procedure as stated above. The reaction of 7-methoxy-1-tetralone oxime (9.00 g, 47.1 mmol) and P2O5 (11.00 g) in methanesulfonic acid (100 mL) gave a crude product which was purified by flash chromatography on silica column with EtOAc/hexane (7:3) as an eluent. Purification procedure provided 6.56 g (73%) of the desired intermediate and 0.27 g of the recovered starting material. M.P.=105-106 C. C11H13NO2 (191.23); MS (EI+) m/e 191 (M)+.
	With polyphosphoric acid; In water; at 115℃; for 0.583333h;	To a solution of 7-methoxy-l-tetralone 55 (5.00 g, 28.4 mmol) in a 1:1 mixture of ethanol and water (70 mL) was added hydroxylamine hydrochloride (2.40 g, 34.1 mmol) and sodium acetate (4.70 g, 56.8 mmol) and the mixture heated to reflux. After 16 h, the reaction mixture was cooled to room temperature and a saturated sodium bicarbonate solution (50 mL) was added. The mixture was extracted with ethyl acetate (3 x 75 mL) and the organic layers were combined, washed with brine (75 mL), dried over sodium sulfate, filtered and concentrated to afford the intermediate oxime (5.4 g), which was directly taken for rearrangement without further purification. The oxime was added to a preheated solution of polyphosphoric acid (60 mL) at 115C and stirred for 5 min. The hot solution was poured into an ice/water mixture and stirred vigorously for 30 min. The precipitated solids were filtered, washed with water (1 L) and dried in a vacuum oven to afford the title compound (56) as an off-white solid: 1H NMR (CDCl3) δ 7.14 (s, IH), 7.11 (s, IH), 6.69 (dd, / = 8.4, 2.6 Hz, IH), 6.50 (d, / = 2.5 Hz, IH), 3.80 (s, 3H), 2.74 (t, / = 7.2 Hz, 2H), 2.35 (t, J= 7.3 Hz, 2H), 2.22-2.18 (m, 2H).

References: [1]Patent: US2018/230084,2018,A1 .Location in patent: Paragraph 0584-0585.
[2]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2573 - 2578.
[3]Journal of the Chemical Society. Perkin transactions I,1997,p. 3261 - 3273.
[4]Patent: US6514965,2003,B1 .
[5]Patent: WO2013/78244,2013,A1 .
[6]Patent: WO2006/103559,2006,A1 .Location in patent: Page/Page column 21; 71.

6
[ 22246-83-9 ]
[ 498557-37-2 ]

References: [1]Archiv der Pharmazie,2002,vol. 335,p. 311 - 317.

7
[ 6836-19-7 ]
[ 22246-83-9 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium azide; PPA; at 55℃;	130a) Combined 7-Methoxy-l-tetralone (5.0 g, 0.028 mol; ) with Polyphosphoric acid (80 g, 0.7 mol; ) in 2-neck 500 ml Flask fit with overhead mechanical stirrer and septa under nitrogen flow. Sodium azide (2.2 g, 0.034 mol; ) added portionwise over 5 min and the reaction was heated to 550C. Continue stirring overnight. The mixture was poured into water and a white precipitate ensued. The mixture was filtered and washed with water then hexane and dried over 6Oh. 8-Methoxy-l ,3,4,5-tetrahydro-benzo[b]azepin-2-oneobtained as a white solid (3.34 g, 62%). MP:103-104ÂC; 1H-NMR (CDC13, 400 MHz) Î' 7.45 (broad s, IH), 7.13 (d, J = 8.3 Hz, IH), 6.72-6.69 (m, IH), 6.54 (d, J = 2.1 Hz, IH), 3.81 (s, 3H), 2.76 (t, J = 7.2 Hz, 2H), 2.38 (t, J = 7.3 Hz, 2H), 2.25-2.18 (m, 2H); LC/MS: 192.07 (M+H).
		Step A: 8-Methoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one Prepared from 7-methoxy-1-tetralone by the procedure described in Example 31, Step A. 1 H NMR (200 MHz, CDCl3): 2.19 (m,2H), 2.32 (m,2H), 2.70 (t,6 Hz,2H), 3.76 (s,3H), 6.57 (d,2 Hz,1H), 6.66 (dd;2,8 Hz;1H), 7.09 (d,8 Hz,1H). FAB-MS: calculated for C11 H13 NO2 191; found 192 (M+H,100%).

References: [1]Patent: WO2008/51547,2008,A1 .Location in patent: Page/Page column 361.
[2]Archiv der Pharmazie,2002,vol. 335,p. 311 - 317.
[3]Journal of the Chemical Society. Perkin transactions I,1997,p. 3261 - 3273.
[4]Patent: US5206235,1993,A .
[5]Australian Journal of Chemistry,2010,vol. 63,p. 211 - 226.
[6]Patent: WO2013/78244,2013,A1 .
[7]Patent: US2018/230084,2018,A1 .
[8]Patent: WO2006/103559,2006,A1 .

8
[ 22246-83-9 ]
[ 362029-07-0 ]

References: [1]Archiv der Pharmazie,2002,vol. 335,p. 311 - 317.

9
[ 22246-83-9 ]
[ 498557-38-3 ]

References: [1]Archiv der Pharmazie,2002,vol. 335,p. 311 - 317.

10
[ 22246-83-9 ]
[ 498557-39-4 ]

References: [1]Archiv der Pharmazie,2002,vol. 335,p. 311 - 317.

11
[ 22246-83-9 ]
[ 498557-40-7 ]

References: [1]Archiv der Pharmazie,2002,vol. 335,p. 311 - 317.

12
[ 22246-83-9 ]
[ 250131-86-3 ]