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Chemical Structure| 22245-96-1 Chemical Structure| 22245-96-1

Structure of 22245-96-1

Chemical Structure| 22245-96-1

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Product Details of [ 22245-96-1 ]

CAS No. :22245-96-1
Formula : C9H8N2O3
M.W : 192.17
SMILES Code : O=C1NCCC2=C1C=C([N+]([O-])=O)C=C2
MDL No. :MFCD08437646
InChI Key :QJSWPNBVJSANQK-UHFFFAOYSA-N
Pubchem ID :13152842

Safety of [ 22245-96-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 22245-96-1 ]

* 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 [ 22245-96-1 ]

[ 22245-96-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 22245-96-1 ]
  • [ 66491-03-0 ]
YieldReaction ConditionsOperation in experiment
98.7% With palladium on activated charcoal; hydrogen; In methanol; for 3h; 7-nitro-3,4-dihydro-isoquinoline -1 (2H) - one (1.88g, 9.8mmol) and Pd / C (190mg) was added to methanol (50 mL), the hydrogenation reaction for 3 hours,Filtration and concentration of the filtrate gave the title compound (1.57 g, yield 98.7%).
86% With hydrogen;palladium 10% on activated carbon; In methanol; under 3102.97 Torr; for 1h; 4C (700 mg, 3.6 mmol) was stirred in MeOH (25 mL) with 10% Pd/C(cat.) under H2 (60 psi) for 1 h. The reaction was filtered through Celite and concentrated in vacuo to give 4D (500 mg, 86% yield). 1H NMR (400 MHz, CD3OD) <n="100"/>delta ppm 2.81 (t, J=6.59 Hz, 2 H) 3.42 (t, J=6.55 Hz, 2 H) 6.84 (dd, J=8.13, 2.42 Hz, 26 H) 7.02 (d, ./=7.91 Hz, 1 H) 7.26 (d, J=2.64 Hz, 1 H).
86% With hydrogen;palladium 10% on activated carbon; In methanol; under 3102.97 Torr; for 1h; Intermediate 1; [00191] Intermediate 1C (700mg, 3.6 mmol) was stirred in MeOH (25ml) with 10% Pd/C (cat.) under H2 (60 psi) for 1 h. The reaction mixture was filtered through Celite and concentrated in vacuo to give Intermediate 1 (500 mg, 86% yield). 1H NMR (400 MHz, CD3OD) delta ppm 2.81 (t, J=6.59 Hz, 2 H) 3.42 (t, J=6.55Hz, 2 H) 6.84 (dd, J=8.13, 2.42 Hz, 26 H) 7.02 (d, J=7.91 Hz, 1 H) 7.26 (d, J=2.64 Hz, 1 H).
With hydrogen;palladium 10% on activated carbon; In methanol; under 2068.65 Torr; A suspension of 7-nitro-3,4-dihydro-2//-isoquinolin-1-one (11.6 g, 60 mmol) and 10%Pd/C (1.2 g,) in MeOH was stirred overnight at RT under H2 (40 psi). The mixture was filtered through Celite and washed with MeOH. The filtrate was evaporated under vacuum to afford 8.2 g of 7-amino-3,4-dihydro-2H-isoquinolin-1-one, which was used without further purification.
With hydrogen;palladium 10% on activated carbon; In methanol; under 2068.65 Torr; A suspension of 7-nitro-3,4-dihydro-2H-isoquinolin-1-one (11.6 g, 60 mmol) and 10% Pd/C (1.2 g), in MeOH was stirred overnight at RT under H2 (40 psi). The mixture was filtered through Celite and washed with MeOH. The filtrate was evaporated under vacuum to afford 8.2 g of 7-amino-3,4-dihydro-2H-isoquinolin-1-one, which was used without further purification.
With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; for 3.5h;Inert atmosphere;Product distribution / selectivity; 10% Pd/C (1 OOmg) was added to a solution of 7-nitro-3,4-dihydro-2H- isoquinolin-l-one (I-24a: 900mg, 4.6875mmol) in methanol (20mL) at room temperature under nitrogen atmosphere. The resulting mixture was hydrogenated at room temperature for 3.5 hours. The reaction was monitored by TLC (100% ethylacetate). The reaction mixture was filtered; the filtrate was concentrated and dried to afford 8 OOmg of the crude product which was used in the next step without further purification.'H NMR (300 MHz, DMSO): 6 7.85-7.63 (bs, 1H), 7.10 (d, 1H), 6.93 (d, 1H), 6.7-6.6 (dd, 1H), 5.15 (s, 2H), 3.35-3.21 (m, 2H), 2.68 (t, 2H)LCMS: 99.94%, m/z = 163.0 (M+l)
With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; under 2068.65 Torr; A suspension of 7-nitro-3,4-dihydro-2H-isoquinolin-l-one (1 1.6 g, 60 mmol) and 10% Pd/C (1.2 g,) in MeOH was stirred overnight at RT under H2 (40 psi). The mixture was filtered through Celite and washed with MeOH. The filtrate was evaporated under vacuum to afford 8.2 g of 7-amino-3,4-dihydro-2H-isoquinolin-l -one, which was used without further purification.
With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 3.5h; Preparation of Intermediate 7-Amino-3,4-dihydro-2H-isoquinolin-1-one (I-32a) 10% Pd/C (100 mg) was added to a solution of 7-nitro-3,4-dihydro-2H-isoquinolin-1-one (I-24a: 900 mg, 4.6875 mmol) in methanol (20 mL) at room temperature under nitrogen atmosphere. The resulting mixture was hydrogenated at room temperature for 3.5 hours. The reaction was monitored by TLC (100% ethylacetate). The reaction mixture was filtered; the filtrate was concentrated and dried to afford 800 mg of the crude product which was used in the next step without further purification. 1H NMR (300 MHz, DMSO): 17.85-7.63 (bs, 1H), 7.10 (d, 1H), 6.93 (d, 1H), 6.7-6.6 (dd, 1H), 5.15 (s, 2H), 3.35-3.21 (m, 2H), 2.68 (t, 2H) LCMS: 99.94%, m/z=163.0 (M+1)
400 mg With hydrogen; Take Intermediate 15 (500mg) was dissolved with 30ml of methanol, was added 1g of Raney-Ni catalyst, under a hydrogen atmosphere and stirred overnight. The reaction mixture was filtered, the filter cake washed with methanol and the combined filtrate 200ml and concentrated to dryness to give a white solid.The solid was isolated by flash chromatography (petroleum ether: ethyl acetate = 1: 1) to give the intermediate 16 (400mg)

 

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