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[ CAS No. 528882-16-8 ]

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Chemical Structure| 528882-16-8
Chemical Structure| 528882-16-8
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Product Details of [ 528882-16-8 ]

CAS No. :528882-16-8 MDL No. :MFCD13677178
Formula : C12H18N2O2 Boiling Point : 347.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :222.28 g/mol Pubchem ID :11492276
Synonyms :

Safety of [ 528882-16-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 528882-16-8 ]

  • Upstream synthesis route of [ 528882-16-8 ]
  • Downstream synthetic route of [ 528882-16-8 ]

[ 528882-16-8 ] Synthesis Path-Upstream   1~7

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YieldReaction ConditionsOperation in experiment
99% With hydrogen In tetrahydrofuran; methanol AROUND bottom flask containing the product of step b (3. 30G, 13. 1MMOL), 10percent palladium on charcoal (300 mg) and THF-MEOH (1: 1/50 ml) was evacuated and flushed with hydrogen three times. The mixture was stirred vigorously overnight under an atmosphere of hydrogen. The catalyst was removed by filtration through a pad of celite and the filtrate evaporated to afford the product as a white solid (2.90g, 99percent). 1H NMR (CDC13) 7.10 (1H, t), 6.62 (2H, m), 6.50 (1H, M), 3.66 (2H, br s), 3.22 (3H, s), 1.46 (9H, s).
99% With hydrogen In tetrahydrofuran; methanol A round bottom flask containing the product of step b (3.30g, 13. 1mmol), 10percent palladium on charcoal (300 mg) and THF-MEOH (1: 1/50 ml) was evacuated and flushed with hydrogen three times. The mixture was stirred vigorously overnight under an atmosphere of hydrogen. The catalyst was removed by filtration through a pad of celite and the filtrate evaporated to afford the product as a white solid (2.90g, 99percent). 1H NMR (CDCl3) 7.10 (1H, t), 6.62 (2H, M3, 6.50 (1H, m), 3.66 (2H, br s), 3.22 (3H, s), 1.46 (9H, S).
97% With palladium on activated charcoal; hydrogen In methanol Triethylamine (30 mL) was added to a solution of tert-butyl methyl-(3-nitrophenyl)-carbamate (500 g, 1.98 mol) in methanol (2.5 L). Palladium on carbon (5percent w/w; Johnson Matthey type 87L paste, 50percent water; 50g) was carefully added under a nitrogen atmosphere and the mixture hydrogenated using a Parr shaker at 50 psi hydrogen pressure. Hydrogen uptake was rapid and the mixture exothermed from 20 °C to 75 °C. Hydrogenation was continued for one hour after the exotherm had ended. TLC (elute 89percent chloroform, 10percent methanol and 1percent ammonia solution) indicated that N3 (Rf=0.75) had been consumed and N4 (Rf=0.55) had formed. The mixture was carefully filtered through a bed of celite on top of a GF-F fibre pad. The filtrate was evaporated under vacuum to dryness. The resulting solid residue was slurried in hexane (1000 mL) for one hour. The mixture was filtered and washed with hexane (500 mL). The product was dried in a vacuum oven at 40 °C to give a tan solid (429 g, 97percent yield). 98.6percent GC purity, melting range = 100—102°C. (This hydrogenation has also been carried out at atmospheric pressure).1H NMR (400 MHz, CDCI3) 57.09 (IH, t, J= 7.9 Hz), 6.65—6.56 (2H, m),6.5 (IH, dd, J= 8.1, 2.0 Hz), 3.65 (2H, brs), 3.22 (3H, s), 1.45 (9H, s).
96% With hydrogen In methanol at 20℃; for 19 h; (iii) Production of tert-butyl (3-aminophenyl)methylcarbamateTo a solution of tert-butyl (3-nitrophenyl)methylcarbamate (40.5 g, 0.161 mol) in ethanol (810 mL) was added 10percent palladium-carbon (4.1 g), and the mixture was stirred at room temperature for 19 hr under a hydrogen atmosphere. The insoluble material was filtered off through celite, and the filtrate was concentrated under reduced pressure. The precipitate was collected by filtration to give the title compound (34.1 g, 96percent) as a colorless powder.1H-NMR (CDCl3, 300 MHz) δ 1.45 (9H, s), 3.22 (3H, s), 3.66 (2H, br s), 6.50 (1H, ddd, J=7.9, 2.3, 0.9 Hz), 6.56-6.66 (2H, m), 7.09 (1H, t, J=7.9 Hz).
91% With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; methanol A round-bottom flask containing tert-butyl methyl(3-nitrophenyl)carbamate (19) (8.8 g, 34.9 mmol), 10percent palladium on charcoal (880 mg), and THF-MeOH (80 mL/80 mL) was evacuated and flushed with hydrogen three times.The mixture was stirred vigorously overnight under an atmosphere of hydrogen. The catalyst was removed by filtration through a pad of Celite, and the filtrate evaporated to afford tert-butyl 3-aminophenyl(methyl)carbamate (20) 7 g as yellow solid (yield 91percent). LC-MS (ESI): m/z (M+1) 223.
4.1 g With palladium on activated charcoal; hydrogen In methanol at 20℃; for 3 h; Autoclave A solution of methyl(3-nitrophenyl)carbamate (6.0 g) in methanol was charged in an autoclave. Pd/C (0.65 g) in methanol was added to reaction mixture. The vessel was pressurized to 5 kg/cm2 H2 pressure and stirred at room temperature for 3 h. After completion of the reaction, the reaction mixture was filtered using Celite and the filter cake was washed with methanol. The filtrate was concentrated under reduced pressure at 40° C. Crude material was purified by using column chromatography. Desired product was eluted with 8percent ethyl acetate in hexane and was concentrated to give 4.1 g of tert-butyl (3-aminophenyl)(methyl)carbamate.
4.1 g With palladium on activated charcoal; hydrogen In methanol at 20℃; for 3 h; Autoclave A solution of methyl(3-nitrophenyl)carbamate (6.0 g) in methanol was charged in an autoclave. Pd/C (0.65 g) in methanol was added to reaction mixture.
The vessel was pressurized to 5 kg/cm2 H2 pressure and stirred at room temperature for 3 h.
After completion of the reaction, the reaction mixture was filtered using Celite and the filter cake was washed with methanol.
The filtrate was concentrated under reduced pressure at 40° C.
Crude material was purified by using column chromatography.
Desired product was eluted with 8percent ethyl acetate in hexane and was concentrated to give 4.1 g of tert-butyl(3-aminophenyl)(methyl)carbamate.

Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2253 - 2261
[2] Patent: WO2004/101533, 2004, A1, . Location in patent: Page 26
[3] Patent: WO2004/98609, 2004, A1, . Location in patent: Page/Page column 24-25
[4] Patent: WO2016/20698, 2016, A1, . Location in patent: Page/Page column 59; 64; 65
[5] Patent: US2011/237620, 2011, A1, . Location in patent: Page/Page column 34-35
[6] Patent: US2013/197014, 2013, A1, . Location in patent: Paragraph 0715; 0718
[7] Patent: US2014/179720, 2014, A1, . Location in patent: Paragraph 0439; 0445
[8] Patent: US2015/174128, 2015, A1, . Location in patent: Paragraph 0690
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Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2253 - 2261
[2] Patent: US2011/237620, 2011, A1,
[3] Patent: US2013/197014, 2013, A1,
[4] Patent: US2014/179720, 2014, A1,
[5] Patent: US2015/174128, 2015, A1,
[6] Patent: WO2016/20698, 2016, A1,
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  • [ 24424-99-5 ]
  • [ 528882-16-8 ]
Reference: [1] Patent: US2011/237620, 2011, A1,
[2] Patent: US2013/197014, 2013, A1,
[3] Patent: US2014/179720, 2014, A1,
[4] Patent: US2015/174128, 2015, A1,
[5] Patent: WO2016/20698, 2016, A1,
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  • [ 99-09-2 ]
  • [ 528882-16-8 ]
Reference: [1] Patent: US2011/237620, 2011, A1,
[2] Patent: US2013/197014, 2013, A1,
[3] Patent: US2014/179720, 2014, A1,
[4] Patent: US2015/174128, 2015, A1,
[5] Patent: WO2016/20698, 2016, A1,
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  • [ 3320-87-4 ]
  • [ 528882-16-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2253 - 2261
  • 6
  • [ 528882-16-8 ]
  • [ 1202759-91-8 ]
Reference: [1] Patent: US2014/179720, 2014, A1,
  • 7
  • [ 528882-16-8 ]
  • [ 1202757-89-8 ]
Reference: [1] Patent: US2014/179720, 2014, A1,
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