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CAS No. : | 6772-65-2 | MDL No. : | MFCD13179355 |
Formula : | C10H11NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 161.20 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With hydrogen; palladium(II) hydroxide; In ethanol; for 24h;Reflux; | To a stirred solution of lactam 4a (636 mg, 4.00 mmol) in EtOH (20mL) was added a catalytic amount of Pd(OH)2 (25 mg, 0.20 mmol) and the mixture was refluxed under a balloon pressure H2 atmosphere for 24 h. The mixture was allowed to cool to r.t. and then it was filtered through a pad of Celite to remove the catalyst and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, 40% EtOAc-PE) to provide 5a as a thick oil; yield: 631 mg (98%). IR (CHCl3): 1643, 1606 cm-1. 1H NMR (200 MHz, CDCl3): delta = 2.99 (t, J = 8 Hz, 2 H), 3.15 (s, 3H), 3.56 (t, J = 8 Hz, 2 H), 7.16 (d, J = 8 Hz, 1 H), 7.25-7.45 (m, 2H), 8.08 (dd, J = 8, 2 Hz, 1 H). 13C NMR (50 MHz, CDCl3): delta = 27.7, 35.0, 48.0, 126.7, 126.8,127.9, 129.2, 131.4, 137.8, 164.6. MS (ESI): m/z (%) = 162.01 (4) [M + H]+. |
With hydrogen;palladium on activated charcoal; In ethanol; | Reference Example 38 2-Methyl-2H-isoquinolin-1-one was subjected to catalytic hydrogenation in a hydrogen atmosphere in ethanol in the presence of palladium/carbon. The resulting compound and concentrated nitric acid were allowed to undergo the reaction in concentrated sulfuric acid. The resulting compound was subjected to catalytic hydrogenation in the same manner as shown in Reference Example 3 to obtain 7-amino-2-methyl-3,4-dihydro-2H-isoquinolin-1-one. NMR2: 2.88 (2 H, t, J = 6.8 Hz), 3.13 (3 H, s), 6.95 (1 H, d, J = 8.0 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With DBN In acetonitrile at 20℃; for 15h; Schlenk technique; Irradiation; | |
77% | With sodium azide; oxygen; potassium carbonate; eosin Y disodium salt In dimethyl sulfoxide at 20℃; for 36h; Irradiation; Green chemistry; | |
63% | With tert.-butylhydroperoxide In 1,4-dioxane; decane at 20℃; for 24h; Irradiation; |
With potassium permanganate In acetonitrile at 25℃; for 2h; | ||
92 %Spectr. | With graphite-supported gold nanoparticles; oxygen; sodium hydrogencarbonate In water; toluene at 110℃; for 24h; | |
Stage #1: 2-methyl-1,2,3,4-tetrahydroisoquinoline With monoamine oxidase variant D9; oxygen In aq. phosphate buffer; N,N-dimethyl-formamide Enzymatic reaction; Stage #2: With E. coli xanthine dehydrogenase In aq. phosphate buffer; N,N-dimethyl-formamide at 37℃; for 6h; Enzymatic reaction; | ||
Multi-step reaction with 2 steps 1: Bromotrichloromethane; potassium carbonate / [D3]acetonitrile / 3 h / 20 °C / Irradiation; Inert atmosphere 2: potassium hexacyanoferrate(III); water / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With sodium hydride In N,N-dimethyl-formamide; mineral oil at 80℃; for 1h; Reflux; | |
Stage #1: 3,4-dihydroisoquinolin-1(2H)-one With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran for 16h; Reflux; | 48.1 2-methyl-3,4-dihydroisoquinolin-1 (211)-one Sodium hydride (408 tug, 10.2 mmol) was added slowly to a stirring solution of 3,4- dihydroisoquinolin-1(211)-one (1.00 g, 6.80 mmol) in THF (30 mL) at 0 °C. The mixturestirred for 0.5 h before methyl iodide (1.45 mg, 10.2 mmol) was added and the mixture was heated to reflux for 16 hours. After cooling to room temperature, water (20 mL) was added and the mixture was extracted with EtOAc (20 mL x 2). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the crude product (1.2 g) as a yellow oil that required no further purification. | |
7.5 g | Stage #1: 3,4-dihydroisoquinolin-1(2H)-one With sodium hydroxide In N,N-dimethyl-formamide for 0.5h; Cooling with ice; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; | 101 2-methyl-3,4-dihydroisoquinoline-1(2H)-one The starting material 3,4-dihydro-isoquinoline -1 (2H) -one (8g, 54.36mmoL) with DMF (100ml) was dissolved, with ice-cooling, was added sodium hydroxide (60%, 3.0g), the resulting mixture was after stirring for 30 minutes, iodomethane (15g, 105.68mmoL).The reaction was stirred overnight at room temperature, poured into ice water, and ethyl acetate (500ml × 3), washed ethyl acetate layer was washed with water, saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give a yellow oil, fast column chromatography (petroleum ether: ethyl acetate = 1: 1) to give the intermediate 23 (7.5g, yellow oil). |
Stage #1: 3,4-dihydroisoquinolin-1(2H)-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Sealed tube; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20 - 80℃; for 1h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tris(2,6-difluorophenyl)borane triethylphosphine oxide; oxalyl dichloride / chloroform / Sealed tube; Inert atmosphere; Glovebox 2: hydrogen; tris(2,6-difluorophenyl)borane triethylphosphine oxide / chloroform / 48 h / 70 °C / 60006 Torr / Autoclave |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: 2-methyl-3,4-dihydro-2H-isoquinolin-1-one With oxalyl dichloride; hydrogen; tris(2,6-difluorophenyl)borane triethylphosphine oxide In chloroform at 70℃; for 48h; Glovebox; Sealed tube; Stage #2: With sodium carbonate In water | 3.1.8 General procedure for FLP-catalyzed hydrogenation of tertiary amides General procedure: In a glovebox B(2,6-F2-C6H3)3 (3c) (3.7 mg, 10.6 μmol, 2.0 mol%, or 9.3 mg, 26.5 μmol, 5.0 mol%) and N,N-disubstituted carboxamide substrate 1 (530 μmol, 1.00 equiv.) were placed in a crimp seal glass vial and dissolved in 3.2 mL abs. CHCl3. Oxalyl chloride (101 mg, 795 μmol, 1.50 equiv.) was subsequently added to the vial. The sample was then transferred to a stainless steel high pressure reactor and charged with hydrogen (80 bar). The reactor was heated with an oil bath at 40 °C to 70 °C for 22 h to 48 h. Subsequently, the reactor was cooled to room temperature and depressurized[SI12]. Purification method for isolation as ammonia salt: The product mixture was filtered through glass wool and the solvent was evaporated under reduced pressure. The crude product was then suspended in Et2O using an ultrasonic bath. The suspension was subsequently centrifuged (3000 rpm for 10 min) and the supernatant solvent was pipetted off. This washing cycle was repeated two times. Finally, the white to lightly colored ammonia salt was dried under reduced pressure and analyzed by NMR spectroscopy and mass spectrometry[SI12]. Purification method for isolation as amine: The product mixture was washed once with sat. aq. Na2CO3. The phases were separated, and the aqueous phase was extracted three times with CHCl3 (when phase separation did not occur, Et2O was added as organic solvent). The combined organic phases were loaded with a small portion of silica and evaporated to dryness. The dry powder was subjected to column chromatography. The colorless to lightly colored amine was subsequently analyzed by NMR spectroscopy and mass spectrometry[SI12]. |