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Quality Control of [ 658082-39-4 ] Purity: 97% SDS Specification

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Product Details of [ 658082-39-4 ]

CAS No. :	658082-39-4
Formula :	C₁₁H₉NO₃
M.W :	203.19
SMILES Code :	O=C(C1=CC2=C(C=C1)C=CNC2=O)OC
English Name :	Methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate
MDL No. :	MFCD18250896
InChI Key :	XPAAMEMUBWBMIK-UHFFFAOYSA-N
Pubchem ID :	60075037

Safety of [ 658082-39-4 ]

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Application In Synthesis of [ 658082-39-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 658082-39-4 ]

[ 658082-39-4 ] Synthesis Path-Downstream 1~14

1
[ CAS Unavailable ]
[ 223671-15-6 ]
[ 658082-39-4 ]

Yield	Reaction Conditions	Operation in experiment
85.4%	With triethylamine In methanol at 100℃; for 20h;	23.1 A solution of 7-bromo-1-hydroxyisoquinoline (2. 00g, 8. [93MMOL)] in MeOH (50mL) was treated with triethylamine (2.6mL, 18.7mmol), and [1,] [1'-] Bis (diphenylphosphino) ferrocene (0.15g, 0. [27MMOL)] in a sealed reactor and heated to [100XB0;C] for 20 hours. The mixture was cooled to room temperature, the tan slurry filtered, the solid washed with MeOH, then ethyl acetate, and dried. This afforded 1.55g of the product as a gray solid (85.4% yield). [H-NMR] [(DMSO-D6)] ; 11.48 (s, [1H),] 8.72 (s, 1H), 8.14-8. 12 (d, 1H), 7.74-7. 72 (d, 1H), 7.31-7. 28 (t, [1H),] 3.86 (s, [3H)] MS: [M+ +1= 204.] 1 Da

References: [1]Current Patent Assignee: WARNER LAMBERT LLC - WO2004/14379, 2004, A1 Location in patent: Page/Page column 112.

2
[ 658082-39-4 ]
[ 100-39-0 ]
[ 1372889-99-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 5h;	3.1 Example 32-benzyl-N-hydroxy-1-oxo-1,2-dihydroisoquinoline-7-carboxamide; Compound I-219 Step 1: methyl 2-benzyl-1-oxo-1,2-dihydroisoquinoline-7-carboxylateTo a solution of methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate (32.5 mg, 0.16 mmol) in DMF (1.50 mL) was added potassium carbonate (66 mg, 0.48 mmol) and benzyl bromide (38.1 μL, 0.32 mmol). The reaction mixture was heated to 60° C. and stirred for 5 h. The mixture was then cooled to rt and concentrated. Water was added and the reaction mixture was extracted with DCM (5 mL, 3×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated to afford methyl 2-benzyl-1-oxo-1,2-dihydroisoquinoline-7-carboxylate. LC-MS: (FA) ES+294.

References: [1]Current Patent Assignee: MILLENNIUM PHARMACEUTICALS - US2012/94997, 2012, A1 Location in patent: Page/Page column 76.

3
[ 658082-39-4 ]
[ 626-15-3 ]
[ 1372890-37-3 ]

Yield	Reaction Conditions	Operation in experiment
42%	With caesium carbonate In N,N-dimethyl-formamide at 20℃;	61.1 Example 612-{3-[(diethylamino)methyl]benzyl}-N-hydroxy-1-oxo-1,2-dihydroisoquinoline-7-carboxamide; Compound I-208 Step 1: methyl 2-[3-(bromomethyl)benzyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxylateTo a solution of methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.15 g, 0.74 mmol) in DMF (7.5 mL) was added cesium carbonate (0.72 g, 2.2 mmol) and 1,3-bis(bromomethyl)benzene (0.29 g, 1.1 mmol). The reaction mixture was stirred at rt overnight. The mixture was diluted with water and extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (0% to 5% EtOAc/DCM) to afford methyl 2-[3-(bromomethyl)benzyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.12 g, 42%). LC-MS: (FA) ES+388.

References: [1]Current Patent Assignee: MILLENNIUM PHARMACEUTICALS - US2012/94997, 2012, A1 Location in patent: Page/Page column 99.

4
[ 658082-39-4 ]
[ 109-64-8 ]
[ 1372890-23-7 ]

Yield	Reaction Conditions	Operation in experiment
38%	Stage #1: methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: 1,3-dibromo-propane In N,N-dimethyl-formamide; mineral oil at 20℃;	44.1 Example 44N-hydroxy-2-[3-(4-methoxyphenoxy)propyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxamide; Compound I-3 Step 1: methyl 2-(3-bromopropyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate; Intermediate-14To a stirred suspension of sodium hydride (60% in mineral oil, 0.30 g, 7.4 mmol) in DMF (15 mL) under an atmosphere of nitrogen cooled to 0° C. was added methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate (1.0 g, 4.9 mmol) in DMF (15 mL) dropwise. The mixture was stirred for 30 mins, then 1,3-dibromopropane (80 μL, 1.28 mmol) was added quickly and the resulting solution was stirred overnight warming to rt slowly. The reaction was quenched with water and extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (0% to 30% EtOAc/hexanes) to afford methyl 2-(3-bromopropyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.60 g, 38%). LC-MS: (FA) ES+326.

References: [1]Current Patent Assignee: MILLENNIUM PHARMACEUTICALS - US2012/94997, 2012, A1 Location in patent: Page/Page column 92.

5
[ 658082-39-4 ]
[ 106-93-4 ]
[ 1372890-25-9 ]

Yield	Reaction Conditions	Operation in experiment
38%	Stage #1: methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.5h; Inert atmosphere; Stage #2: ethylene dibromide In N,N-dimethyl-formamide; mineral oil	46.1 Example 46N-hydroxy-2-[2-(4-methoxyphenoxy)ethyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxamide; Compound I-257 Step 1: methyl 2-(2-bromoethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate; Intermediate-15To a stirred suspension of sodium hydride (60% in mineral oil, 0.81 g, 20.2 mmol) in DMF (30 mL) under an atmosphere of nitrogen was added methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate (2.05 g, 10.1 mmol) in DMF (20 mL) dropwise. The mixture was stirred for 30 mins, then 1,2-dibromoethane (8.7 mL, 101 mmol) was added quickly and the resulting solution was stirred for 2 h. The reaction was quenched with water and extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (0% to 40% EtOAc/hexanes) to afford methyl 2-(2-bromoethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (1.20 g, 38%). LC-MS: (FA) ES+311.

References: [1]Current Patent Assignee: MILLENNIUM PHARMACEUTICALS - US2012/94997, 2012, A1 Location in patent: Page/Page column 93.

6
[ 658082-39-4 ]
[ 106-93-4 ]
[ 1372890-35-1 ]

Yield	Reaction Conditions	Operation in experiment
65%	With caesium carbonate In acetonitrile at 20℃; for 24h;	58.1 Example 58N-hydroxy-2-(2-hydroxyethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxamide; Compound I-158 Step 1: methyl 2-(2-hydroxyethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylateTo a solution of methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate (1.26 g, 6.2 mmol) dissolved in acetonitrile (100 mL) was added 1,2-dibromoethane (5.3 mL, 62 mmol) and cesium carbonate (8.1 g, 24.8 mmol). The reaction mixture was stirred at rt for 1 d. The mixture was then concentrated, diluted with water and extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (50% to 100% EtOAc/hexanes) to afford methyl 2-(2-hydroxyethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (1.0 g, 65%). LC-MS: (FA) ES+248

References: [1]Current Patent Assignee: MILLENNIUM PHARMACEUTICALS - US2012/94997, 2012, A1 Location in patent: Page/Page column 98.

7
[ 4360-63-8 ]
[ 658082-39-4 ]
[ 1372890-31-7 ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium carbonate In N,N-dimethyl-formamide at 140℃; for 5h;	54.1 Example 54N-hydroxy-2-{2-[(4-methoxyphenyl)amino]ethyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxamide; Compound I-97 Step 1: methyl 2-(1,3-dioxolan-2-ylmethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylateTo a solution of methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.5 g, 1.72 mmol) in DMF (10 mL) was added potassium carbonate (1.2 g, 8.6 mmol) and 2-(bromomethyl)-1,3-dioxolane (0.62 mL, 6.03 mmol). The reaction mixture was heated at 140° C. and stirred for 5 h. The mixture was cooled to rt, water was added and the mixture was extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (0% to 50% EtOAc/hexanes) to afford methyl 2-(1,3-dioxolan-2-ylmethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.32 g, 64%). LC-MS: (FA) ES+290.

References: [1]Current Patent Assignee: MILLENNIUM PHARMACEUTICALS - US2012/94997, 2012, A1 Location in patent: Page/Page column 96.

8
[ 658082-39-4 ]
[ 1372888-25-9 ]

Yield	Reaction Conditions	Operation in experiment
37%	With hydroxylamine hydrochloride; potassium hydroxide In methanol at 20 - 90℃; for 1.5h; Inert atmosphere;	2 Example 2N-hydroxy-1-oxo-1,2-dihydroisoquinoline-7-carboxamide; Compound I-232 A mixture of hydroxylamine hydrochloride (2.0 g, 29 mmol) in methanol (10 mL) was heated at 90° C. under a dry nitrogen atmosphere until homogeneous. To this heated solution was added a solution of potassium hydroxide (2.85 g, 50.8 mmol) in methanol (6 mL). A precipitate formed on mixing. After heating at 90° C. for 30 minutes, the mixture was cooled to rt and the solids were allowed to settle. The resulting solution was assumed to contain 1.7 M hydroxylamine.potassium salt and was carefully removed by syringe to exclude solids. An aliquot of the above solution (1.0 mL, 1.7 mmol) was added to a solution of methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate (32.5 mg, 0.16 mmol) in methanol (1 mL). After stirring for 1 h at rt, excess reagent was quenched by the addition of acetic acid (0.20 mL, 3.52 mmol). The mixture was concentrated to dryness and the residue was twice co-evaporated with toluene. The crude product was purified by preparative HPLC to afford N-hydroxy-1-oxo-1,2-dihydroisoquinoline-7-carboxamide (12 mg, 37%). LC-MS: (FA) ES+205; 1H NMR (300 MHz, MeOD) δ 8.67 (d, J=1.5 Hz, 1H), 8.06 (dd, J=8.3, 1.9 Hz, 1H), 7.73 (d, J=8.4 Hz, 1H), 7.26 (d, J=7.1 Hz, 1H), 6.70 (d, J=7.3 Hz, 1H).

References: [1]Current Patent Assignee: MILLENNIUM PHARMACEUTICALS - US2012/94997, 2012, A1 Location in patent: Page/Page column 75-76.

9
[ 658082-39-4 ]
[ 1372890-24-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: 20 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 40 °C