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[ CAS No. 28694-94-2 ]

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Chemical Structure| 28694-94-2
Chemical Structure| 28694-94-2
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Product Details of [ 28694-94-2 ]

CAS No. :28694-94-2 MDL No. :MFCD16620323
Formula : C9H10N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :210.19 g/mol Pubchem ID :-
Synonyms :

Safety of [ 28694-94-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 28694-94-2 ]

  • Downstream synthetic route of [ 28694-94-2 ]

[ 28694-94-2 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 28694-94-2 ]
  • [ 181765-85-5 ]
  • [ 755026-46-1 ]
  • 4
  • [ 28694-94-2 ]
  • [ 755027-09-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 87 percent / dppf; Cs2CO3 / Pd(OAc)2 / 16 h / 95 °C 2: H2 / Pt/C / methanol / 20 °C 3: TsOH*H2O / toluene / 48 h / Heating 4: 78 percent / Cy-MAP; CsF / Pd(OAc)2 / 1,2-dimethoxy-ethane; methanol / 12 h / Heating
  • 5
  • [ 28694-94-2 ]
  • [ 755027-44-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 87 percent / dppf; Cs2CO3 / Pd(OAc)2 / 16 h / 95 °C 2: H2 / Pt/C / methanol / 20 °C 3: TsOH*H2O / toluene / 48 h / Heating 4: 78 percent / Cy-MAP; CsF / Pd(OAc)2 / 1,2-dimethoxy-ethane; methanol / 12 h / Heating 5: LiOH*H2O / methanol / Heating
  • 6
  • [ 28694-94-2 ]
  • 2-[3-(3-methoxy-4-nitrophenyl)-11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-8-yl]-N,N-dimethylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 87 percent / dppf; Cs2CO3 / Pd(OAc)2 / 16 h / 95 °C 2: H2 / Pt/C / methanol / 20 °C 3: TsOH*H2O / toluene / 48 h / Heating 4: 78 percent / Cy-MAP; CsF / Pd(OAc)2 / 1,2-dimethoxy-ethane; methanol / 12 h / Heating 5: LiOH*H2O / methanol / Heating 6: 62 mg / HATU; Et3N / dimethylformamide
  • 7
  • [ 28694-94-2 ]
  • 2-[3-(3-methoxy-4-nitro-phenyl)-11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-8-yl]N[4-(4-morpholinyl)phenyl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 87 percent / dppf; Cs2CO3 / Pd(OAc)2 / 16 h / 95 °C 2: H2 / Pt/C / methanol / 20 °C 3: TsOH*H2O / toluene / 48 h / Heating 4: 78 percent / Cy-MAP; CsF / Pd(OAc)2 / 1,2-dimethoxy-ethane; methanol / 12 h / Heating 5: LiOH*H2O / methanol / Heating 6: HATU; Et3N / dimethylformamide
  • 8
  • [ 123270-23-5 ]
  • [ 28694-94-2 ]
YieldReaction ConditionsOperation in experiment
89% With hydrogenchloride In water for 48h; 6.6A Example 6; methyl (3-chloro-11-oxo-10, 11-dihydro-5h-dibenzorb, elfl, 4ldiazepin-8-yl) acetate; Example 6A; methyl (4-amino-3-nitrophenyl)acetate A mixture of N- [4- (cyanomethyl)-2-nitrophenyl] acetamide (4.8 g), concentrated HC1 (100 mL), and water (300 ML) was heated to reflux for two days, cooled to room temperature, and concentrated to near dryness under vacuum. The concentrate was treated with methanol (300 mL) and concentrated H2SO4 (30 mL), heated to reflux overnight, and concentrated under vacuum to remove the methanol. The residue was partitioned between ethyl acetate and water and the organic layers were combined, washed with saturated NAHC03 and brine, dried (MGS04), and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 7: 3 hexanes/ethyl acetate to provide 4. 1G (89%) of the desired product. MS (DCI) m/e 211 (M+H) +, 228 (M+NH4) + ; 1H NMR (300 MHz, DMSO-D6) 8 7.88 (d, J = 2 Hz, 1H), 7.39 (s, 2H), 7.30 (dd, J = 8.5, 2 Hz, 1H), 6.97 (d, J = 8.4 Hz, 1H), 3.61 (s, 3H).
  • 9
  • [ 28694-94-2 ]
  • [ 64-18-6 ]
  • [ 473895-86-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: methyl 2-(4-amino-3-nitrophenyl)acetate With hydrogen In methanol at 20℃; for 6h; Stage #2: formic acid at 100℃; for 5h; 3 Preparation 3; 1H-Benzimidazol-6-ylacetic Acid 1.9 g (9.04 mmol) of methyl (4-amino-3-nitrophenyl)acetate (J. Med. Chem., 1997, 40(7), 1049) are dissolved in 300 ml of methanol, and 480 mg of 10% Pd/C are added thereto. Hydrogenation is carried out at ambient temperature for 6 hours, the catalyst is filtered off and the solvent is evaporated under reduced pressure. 1.6 g of oil are thus obtained, which oil is dissolved in 18 ml of 98% formic acid and is heated at 100° C. for 5 hours. The solvent is subsequently evaporated under reduced pressure and 1.6 g of the title product are thus obtained. [0102] Thin layer chromatography (eluent: ethyl acetate/methanol=1/1): Rf 0.35.
Stage #1: methyl 2-(4-amino-3-nitrophenyl)acetate With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 6h; Stage #2: formic acid In water at 100℃; for 5h;
  • 10
  • [ 39552-81-3 ]
  • [ 28694-94-2 ]
YieldReaction ConditionsOperation in experiment
55% With nitric acid; trifluoroacetic acid; at -10 - 20℃; for 18h; methyl 2-(4-aminophenyl)acetate (17.70 g, 107.0 mmol) was dissolved in TFA (red dark solution) and cooled to -10C. Then fuming HNO3 (4.76 mL, 112.0 mmol) was added dropwise. The reaction mixture was warmed to rt and stirred for 18 h. TFA was evaporated and the residue was neutralized with sat.NaHCO3 and solid NaHCO3. The aqueous layer was extracted with EtOAc. The organic layer was dried over Mg504, filtered and the solution was concentrated to dryness. The crude material was purified by silica gel column chromatography eluting with heptane and a gradient of heptane/EtOAc from [100:0] to [80:20] to afford the desired product (12.30 g, 55%) as yellow solid.1H NMR (300 MHz, CDCI3, d in oom): 3.55 (s, 2H), 3.71 (s, 3H), 6.04 (s, 2H), 6.79 (d, 1H, J=8.6Hz), 7.31 (dd, 1H, J=8.5Hz, J=1.8Hz), 8.02 (s, 1H).
18% N-((4-chloro-2-methylphenyl)(phenyl)methyl)-2-(2-(2-methylpyridin-3-yl)-lH-benzo[a) methyl 2-(4-amino-3-nitrophenyl)acetateFuming EtaNuOmicron3 (3 mL) was added dropwise to a solution of methyl 2-(4- aminophenyl)acetate (6.0 g, 36.32 mmol) in glacial AcOH (200 mL) at 0 C. The reaction mixture was allowed to warm to rt and then heated to 100 C for 6 h. The reaction mixture was cooled to rt, concentrated under reduced pressure and azeotroped with toluene. The reaction mixture was neutralized using 10% aq. NaOH and extracted with EtO Ac. The organic layer was washed with water and brine, dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure. The resultant residue was purified by column chromatography (20% EtO Ac/petroleum ether) to afford the title compound (1.4 g, 18%) as an orange solid. TLC: 50% EtOAc/petroleum ether, Rf= 0.5. lH NMR (400 MHz, DMSO-d6) delta ppm 7.88 (d, J= 1.8 Hz, 1H), 7.41 (br s, 2H), 7.31 (dd, J= 8.9, 2.1 Hz, 1H), 6.97 (d, J= 8.5 Hz, 1H), 3.61 (m, 5H
  • 11
  • [ 28694-94-2 ]
  • [ 257632-89-6 ]
YieldReaction ConditionsOperation in experiment
89.5% With palladium 10% on activated carbon; hydrogen In methanol at 25℃; for 3h; 20.B Step B methyl 2- (3, 4-diaminophenyl) acetate To a solution of methyl 2- (4-amino-3-nitro-phenyl) acetate (500 mg, 2.38 mmol) in MeOH (5 mL) was added Pd/C (0.2 g, 10%purity) . The mixture was stirred at 25 under H2 (15 Psi) for 3 hrs. The mixture was filtered, and the filtrate was concentrated in vacuo and the residue was purified by flash chromatography (PE/EtOAc = 1/1) to give methyl 2- (3, 4-diaminophenyl) acetate (384 mg, 89.5%yield) as a brown oil. 1H NMR (400 MHz, DMSO-d6) δ 6.44 -6.37 (m, 2H) , 6.25 (d, J = 6.8, 1H) , 4.43 -4.35 (m, 4H) , 3.56 (s, 3H) , 3.34 (s, 2H) .
89.5% With palladium 10% on activated carbon; hydrogen In methanol at 25℃; for 3h; 20.B Step B methyl 2- (3, 4-diaminophenyl) acetate To a solution of methyl 2- (4-amino-3-nitro-phenyl) acetate (500 mg, 2.38 mmol) in MeOH (5 mL) was added Pd/C (0.2 g, 10%purity) . The mixture was stirred at 25 under H2 (15 Psi) for 3 hrs. The mixture was filtered, and the filtrate was concentrated in vacuo and the residue was purified by flash chromatography (PE/EtOAc = 1/1) to give methyl 2- (3, 4-diaminophenyl) acetate (384 mg, 89.5%yield) as a brown oil. 1H NMR (400 MHz, DMSO-d6) δ 6.44 -6.37 (m, 2H) , 6.25 (d, J = 6.8, 1H) , 4.43 -4.35 (m, 4H) , 3.56 (s, 3H) , 3.34 (s, 2H) .
73% With palladium 10% on activated carbon; hydrogen In methanol for 4h; 23.b b) methyl 2-(3,4-diaminophenyl)acetate Methyl 2-(4-amino-3-nitrophenyl)acetate (800 mg, 3.81 mmol) was hydrogenated using 10% Pd/C (120 mg) in MeOH (80 mL) under H2 balloon pressure for 4 h. The reaction mixture was filtered through Celite and washed through with MeOH. The solvent was concentrated to obtain the title compound (500 mg, 73%). TLC: 100% EtOAc, Rf= 0.3. lB NMR (300 MHz, DMSO-d6) δ ppm 6.41 - 6.37 (m, 2H), 6.24 - 6.21 (m, 1H), 4.43 - 4.35 (m, 4H), 3.55 (s, 5H).
  • 12
  • [ 28694-94-2 ]
  • [ 1422169-96-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: palladium 10% on activated carbon; hydrogen / methanol / 4 h 2.1: sodium hydrogensulfite / ethanol / 0.5 h / 20 °C 2.2: 4 h / 90 °C
  • 13
  • [ 28694-94-2 ]
  • [ 17118-74-0 ]
  • [ 121-44-8 ]
  • methyl 2-(4-(ethylcarbamoylformyl)-3-nitrophenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In dichloromethane at 0 - 20℃; for 18h; 1a.2 Step 2 to a solution of methyl 2-(4-amino-3-nitrophenyl)acetate Ex.lla (1.50 g, 7.14 mmol) in CH2CI2 (28 mL) and triethylamine (2.25 mL, 10.71 mmol) was added dropwise ethyl oxalylchloride (1.47 mL, 12.84 mmol) at 000. The reaction mixture was stirred at rt for 18 h. The reaction was quenched with brine. The aqueous layer was extracted with EtOAc. The organic layer was dried overMg504, filtered and the solution was concentrated to dryness. The crude material was purified by silica gel column chromatography eluting with heptane and a gradient of heptane/EtOAc from [100:0] to [70:30] to give methyl 2-(4- (ethyl carbamoylformyl)-3-n itrophenyl)acetate (1.55 g, 70%).- 1H NMR (300 MHz, DMSO-d6, din ppm): 1.33 (t, 3H, J=7.lHz), 3.61 (s, 3H), 3.65 (s, 2H), 4.34 (d, 2H, J=7.lHz), 7.70 (d, 1H, J=8.6Hz), 8.01 (d, 1H, J=8.4Hz), 8.08 (s, 1 H), 11.35 (s, 1 H).
  • 14
  • [ 28694-94-2 ]
  • 2-(2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-6-yl)-N-{phenyl[2-(piperidin-1-yl)phenyl]methyl}acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dichloromethane / 18 h / 0 - 20 °C 2: acetic acid; iron / 4 h 3: lithium hydroxide monohydrate; water / tetrahydrofuran / 5 h / 0 °C 4: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 2 h / 20 °C
  • 15
  • [ 28694-94-2 ]
  • 2-(2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-6-yl)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dichloromethane / 18 h / 0 - 20 °C 2: acetic acid; iron / 4 h 3: lithium hydroxide monohydrate; water / tetrahydrofuran / 5 h / 0 °C
  • 16
  • [ 28694-94-2 ]
  • methyl 2-(1,2,3,4-tetrahydro-2,3-dioxoquinoxalin-7-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloromethane / 18 h / 0 - 20 °C 2: acetic acid; iron / 4 h
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