Structure of 88014-09-9
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| CAS No. : | 88014-09-9 |
| Formula : | C13H17NO2 |
| M.W : | 219.28 |
| SMILES Code : | O=C(OCC)CN1CC2=C(C=CC=C2)CC1 |
| English Name : | Ethyl 2-(3,4-dihydroisoquinolin-2(1H)-yl)acetate |
| MDL No. : | MFCD00977193 |
* 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 |
|---|---|---|
| 68% | With lithium aluminium tetrahydride In diethyl ether for 3h; Reflux; | |
| 54.5% | With lithium aluminium tetrahydride In diethyl ether for 3h; Heating; | |
| With sodium hydroxide; LiAlH4 In tetrahydrofuran; dichloromethane; water | 2-(2-hydroxyethyl)-1,2,3,4-tetrahydroisoquinoline 2-(2-hydroxyethyl)-1,2,3,4-tetrahydroisoquinoline 1.9 g (50.0 mmol) of LiAlH4 were suspended, under nitrogen atmosphere, in 100 ml of dry THF; the reaction mixture was cooled at 0° C. and 5.0 g (22.8 mmol) of 2-ethoxycarbonylmethyl-1,2,3,4-tetrahydroisoquinoline (compound of Description 14), dissolved in 100 ml of dry THF, were added dropwise. The reaction was stirred at room temperature for 2 hours, ice-cooled and quenched with 2.5 ml of H2O, 7.5 ml of 15% NaOH, 2.5 ml of H2O, stirred for 30 minutes and filtered. The filtrate was evaporated in vacuo to dryness, dissolved in CH2Cl2 and washed with sat. sol. NaCl. The organic layer was dried over Na2SO4 and evaporated in vacuo to dryness to yield 3.9 g of the title compound which was used without further purification. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydrogenchloride |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 98% | With sodium hydroxide; water In methanol at 48℃; | 199.2 Step 2. Preparation of (3, 4-DIHYDRO-1H-ISOQUINOLIN-2-YL)-ACETIC acid 199 (b) To a suspension of Intermediate 199 (a) (1.643 g, 7.5 MMOL) in methanol (20 mL) was added 2.5 N NAOH (7.8 mL). The reaction solution was heated at 48 °C and stirred overnight. With cooling, the pH was adjusted to 8 by adding 1M HCI. The volatile components were removed under vacuum, and the resulting mixture was suspended in methanol. After filtration to remove the insoluble solids, the filtrate was evaporated to give Intermediate 199 (b) (1.4 G, 7.3 MMOL) as white foam in 98% yield. 'H-NMR (d6-DMSO) : No. 7.13-7. 09 (m, 3H), 7.02 (t, 1H), 3.76 (s, 2H), 3.27 (s, 2H), 2.88-2. 82 (m, 4H). LCMS: (M+H+) 192.2. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 85% | With N-hydroxyphthalimide; oxygen; copper(I) bromide In acetonitrile at 60℃; Inert atmosphere; Green chemistry; | |
| 77% | With tert.-butylhydroperoxide; copper(ll) bromide In toluene at 50℃; for 48h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 80% | With N-hydroxyphthalimide; oxygen; copper(I) bromide In acetonitrile at 60℃; Inert atmosphere; Green chemistry; | |
| 60% | With tert.-butylhydroperoxide; copper(ll) bromide In toluene at 50℃; for 48h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 95% | Stage #1: N-(4-methoxyphenyl)maleimide; (3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid ethyl ester With tert.-butylhydroperoxide; Rh2(cap)4*2CH3CN; potassium carbonate In decane; acetonitrile Stage #2: With N-Bromosuccinimide In decane; acetonitrile for 1h; | General experimental procedure: General procedure: Rh2(cap)42CH3CN(0.0015mmol),tetrahydroisoquinoline 1(0.36mmol),and K2CO3(0.15mmol)inCH3CN(2.0mL)were mixed and kept under stirring while t-BuOOH (5.5Mindecane,0.60 mmol)was added inone portion atroom temperature.Then N-phenylmaleimide 2(0.30mmol)inCH3CN(1.0mL)was added dropwise over 2husing asyringe pump.The reaction was stirred until substrate 2was completely consumed (ca.3h),and then N-bromosuccinimide (0.60mmol)was added and stirring continued for 1h.Saturated NaHSO 3(5mL)was added toquench the reaction.The crude mixture was extracted with CH2Cl2(10mL3),and the combined organic phases were dried over sodium sulfate andfiltered.The filtratewas concentrated and the residue purifiedbyflashcolumnchromatography onsilica gel using petroleum ether-dichloromethane-ethyl acetate asthe eluent,giving the desired product 3.The structures ofthe cycloadducts3a-lwere identifiedbycomparison with the1HNMR spectra inRef.4and confirmedbymass spectra. |
| 91% | With N-Bromosuccinimide; C88H30BF2N3 In dichloromethane at 20℃; for 1h; Irradiation; | |
| 87% | With dihydrogen peroxide; iodine In water; N,N-dimethyl-formamide at 80℃; for 6h; |
| 87.3% | Stage #1: N-(4-methoxyphenyl)maleimide; (3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid ethyl ester With oxygen In dichloromethane at 20℃; for 2h; Irradiation; Stage #2: With N-Bromosuccinimide at 20℃; for 1h; | |
| 86% | With N-hydroxyphthalimide; oxygen; copper(I) bromide In acetonitrile at 60℃; Inert atmosphere; Green chemistry; | |
| 83% | Stage #1: N-(4-methoxyphenyl)maleimide; (3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid ethyl ester In acetonitrile at 20℃; for 2h; Irradiation; Stage #2: With N-Bromosuccinimide In acetonitrile at 20℃; for 0.166667h; | |
| 81% | Stage #1: N-(4-methoxyphenyl)maleimide; (3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid ethyl ester With [Ru(bpy)3]Cl2; oxygen In acetonitrile at 20℃; for 12.5h; Irradiation; Stage #2: With N-Bromosuccinimide In acetonitrile at 20℃; for 1h; | |
| 75% | With N-Bromosuccinimide In acetonitrile at 20℃; for 1h; UV-irradiation; | |
| 74% | With tert.-butylhydroperoxide; potassium iodide In water; N,N-dimethyl-formamide at 80℃; for 9h; Green chemistry; | |
| 72% | With N-Bromosuccinimide; C65H61BF2I2N7O3(1+) In dichloromethane for 1.5h; Irradiation; | |
| 70% | With N-Bromosuccinimide; C80H68B3F6I2N13O4; oxygen In dichloromethane at 20℃; for 1.5h; Irradiation; | |
| 64% | With tert.-butylhydroperoxide; copper(ll) bromide In toluene at 50℃; for 48h; | |
| 88 %Chromat. | With cadmium sulphide In neat (no solvent) at 20℃; for 18h; Irradiation; Green chemistry; | |
| Multi-step reaction with 2 steps 1: JNU-204; oxygen / acetonitrile / 12 h / 20 °C / Irradiation 2: N-Bromosuccinimide / acetonitrile / 1 h | ||
| 74% | Stage #1: N-(4-methoxyphenyl)maleimide; (3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid ethyl ester With oxygen; [5,6]fullerene-C70 In toluene at 20℃; Microwave irradiation; Sealed tube; Stage #2: With N-Bromosuccinimide In toluene |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 97% | Stage #1: N-(4-nitrophenyl)maleimide; (3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid ethyl ester With tert.-butylhydroperoxide; Rh2(cap)4*2CH3CN; potassium carbonate In decane; acetonitrile Stage #2: With N-Bromosuccinimide In decane; acetonitrile for 1h; | General experimental procedure: General procedure: Rh2(cap)42CH3CN(0.0015mmol),tetrahydroisoquinoline 1(0.36mmol),and K2CO3(0.15mmol)inCH3CN(2.0mL)were mixed and kept under stirring while t-BuOOH (5.5Mindecane,0.60 mmol)was added inone portion atroom temperature.Then N-phenylmaleimide 2(0.30mmol)inCH3CN(1.0mL)was added dropwise over 2husing asyringe pump.The reaction was stirred until substrate 2was completely consumed (ca.3h),and then N-bromosuccinimide (0.60mmol)was added and stirring continued for 1h.Saturated NaHSO 3(5mL)was added toquench the reaction.The crude mixture was extracted with CH2Cl2(10mL3),and the combined organic phases were dried over sodium sulfate andfiltered.The filtratewas concentrated and the residue purifiedbyflashcolumnchromatography onsilica gel using petroleum ether-dichloromethane-ethyl acetate asthe eluent,giving the desired product 3.The structures ofthe cycloadducts3a-lwere identifiedbycomparison with the1HNMR spectra inRef.4and confirmedbymass spectra. |
| 87.1% | Stage #1: N-(4-nitrophenyl)maleimide; (3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid ethyl ester With oxygen In dichloromethane at 20℃; for 2h; Irradiation; Stage #2: With N-Bromosuccinimide at 20℃; for 1h; | |
| 84% | With N-Bromosuccinimide; C88H30BF2N3 In dichloromethane at 20℃; for 1h; Irradiation; |
| 81% | With dihydrogen peroxide; iodine In water; N,N-dimethyl-formamide at 80℃; for 6h; | |
| 81% | With tert.-butylhydroperoxide; potassium iodide In water; N,N-dimethyl-formamide at 80℃; for 9h; Green chemistry; | |
| 80% | With N-Bromosuccinimide; C80H68B3F6I2N13O4; oxygen In dichloromethane at 20℃; for 1.5h; Irradiation; | |
| 72% | With N-Bromosuccinimide In acetonitrile at 20℃; for 1h; UV-irradiation; | |
| 68% | Stage #1: N-(4-nitrophenyl)maleimide; (3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid ethyl ester With [Ru(bpy)3]Cl2; oxygen In acetonitrile at 20℃; for 12.5h; Irradiation; Stage #2: With N-Bromosuccinimide In acetonitrile at 20℃; for 1h; | |
| 53% | With N-Bromosuccinimide; C65H61BF2I2N7O3(1+) In dichloromethane for 1.5h; Irradiation; | |
| 79 %Chromat. | With cadmium sulphide In neat (no solvent) at 20℃; for 24h; Irradiation; Green chemistry; |
