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[ CAS No. 425645-31-4 ] {[proInfo.proName]}

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Chemical Structure| 425645-31-4
Chemical Structure| 425645-31-4
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Product Details of [ 425645-31-4 ]

CAS No. :425645-31-4 MDL No. :MFCD02221168
Formula : C12H9NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :231.20 Pubchem ID :-
Synonyms :

Safety of [ 425645-31-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 425645-31-4 ]

* 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 [ 425645-31-4 ]

[ 425645-31-4 ] Synthesis Path-Downstream   1~21

  • 1
  • [ 425645-31-4 ]
  • [ 1045704-64-0 ]
YieldReaction ConditionsOperation in experiment
96% With aluminum (III) chloride; sodium tetrahydroborate In tetrahydrofuran at -10℃; Reflux; General procedure for synthesis of compounds 9a-h. General procedure: To the cooled (-10 °C) solution of carbonyl compound 16 (40 mmol) in dry THF (100 mL) anhydrous AlCl3 (9.58 g, 72 mmol) was added by portions under stirring. Then NaBH4 (2.74 g, 72 mmol) was added. Reaction mixture was refluxed for 1-2 h (TLC control) and poured into water (800 mL). Product was extracted with Et2O (3 x 100 mL). The combined ether extracts were dried with anhydrous Na2SO4, refluxed with activated charcoal, filtered and evaporated to dryness. The obtained compounds were used without additional purification except compounds 9a,c which were recrystallized from Et2O-hexane mixture to characterize examples of compounds 9.
60% With aluminum (III) chloride; sodium tetrahydroborate In tetrahydrofuran Cooling; Reflux;
With sodium tetrahydroborate; aluminium trichloride In tetrahydrofuran Heating;
  • 2
  • [ 98-01-1 ]
  • [ 89-62-3 ]
  • [ 425645-31-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-methyl-2-nitroaniline With hydrogenchloride In water at 80℃; for 0.5h; Stage #2: With sodium nitrite In water at -10 - 0℃; for 0.666667h; Stage #3: furfural In water; acetone at 20℃; for 12h;
Stage #1: 4-methyl-2-nitroaniline With hydrogenchloride; water at 80℃; for 0.5h; Stage #2: With sodium nitrite In water at -5 - 0℃; for 0.666667h; Stage #3: furfural With copper dichloride In water; acetone at 20℃; for 12h;
  • 3
  • [ 425645-31-4 ]
  • [ 1045704-68-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: AlCl3; NaBH4 / tetrahydrofuran / Heating 2: hydrazin hydrate / Raney nickel / ethanol / Heating
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; aluminum (III) chloride / tetrahydrofuran / -10 °C / Reflux 2: hydrazine hydrate / ethanol / 2 h / Reflux
  • 4
  • [ 425645-31-4 ]
  • [ 900530-19-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AlCl3; NaBH4 / tetrahydrofuran / Heating 2: hydrazin hydrate / Raney nickel / ethanol / Heating 3: pyridine / cooling
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; aluminum (III) chloride / tetrahydrofuran / -10 °C / Reflux 2: hydrazine hydrate / ethanol / 2 h / Reflux 3: pyridine / 12 h / 0 - 20 °C
  • 5
  • [ 425645-31-4 ]
  • [ 400750-84-7 ]
  • [ 1219474-98-2 ]
YieldReaction ConditionsOperation in experiment
65% With hydrogenchloride In water; acetic acid at 30 - 35℃; for 1.5h;
  • 6
  • [ 425645-31-4 ]
  • [ 1352548-41-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: piperidine / ethanol / 0.08 h / Reflux 2.1: sodium tetrahydroborate / ethanol / 0.17 h / Reflux 2.2: pH 7 / Cooling 3.1: hydrogenchloride; water; acetic acid / 0.67 h / Reflux 3.2: 0.5 h / Reflux 3.3: 20 °C
  • 7
  • [ 425645-31-4 ]
  • [ 1352548-09-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: piperidine / ethanol / 0.08 h / Reflux 2.1: sodium tetrahydroborate / ethanol / 0.17 h / Reflux 2.2: pH 7 / Cooling 3.1: hydrogenchloride; water; acetic acid / 0.67 h / Reflux 3.2: 0.5 h / Reflux 3.3: 20 °C 4.1: potassium hydroxide / dimethyl sulfoxide / 0.33 h / 20 °C
  • 8
  • [ 425645-31-4 ]
  • [ 1352548-13-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: piperidine / ethanol / 0.08 h / Reflux 2.1: sodium tetrahydroborate / ethanol / 0.17 h / Reflux 2.2: pH 7 / Cooling 3.1: hydrogenchloride; water; acetic acid / 0.67 h / Reflux 3.2: 0.5 h / Reflux 3.3: 20 °C 4.1: potassium hydroxide / dimethyl sulfoxide / 0.33 h / 20 °C 5.1: hydrazine hydrate / ethanol / 2 h / Reflux
  • 9
  • [ 425645-31-4 ]
  • [ 1352548-20-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: piperidine / ethanol / 0.08 h / Reflux 2.1: sodium tetrahydroborate / ethanol / 0.17 h / Reflux 2.2: pH 7 / Cooling 3.1: hydrogenchloride; water; acetic acid / 0.67 h / Reflux 3.2: 0.5 h / Reflux 3.3: 20 °C 4.1: potassium hydroxide / dimethyl sulfoxide / 0.33 h / 20 °C 5.1: hydrazine hydrate / ethanol / 2 h / Reflux 6.1: pyridine / 12 h / 0 - 20 °C
  • 10
  • [ 425645-31-4 ]
  • [ 1352548-21-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; aluminum (III) chloride / tetrahydrofuran / -10 °C / Reflux 2: hydrazine hydrate / ethanol / 2 h / Reflux 3: pyridine / 12 h / 0 - 20 °C
  • 11
  • [ 425645-31-4 ]
  • [ 1352548-22-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; aluminum (III) chloride / tetrahydrofuran / -10 °C / Reflux 2: hydrazine hydrate / ethanol / 2 h / Reflux 3: benzene / 1 h / 20 °C
  • 12
  • [ 425645-31-4 ]
  • [ 1352548-23-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; aluminum (III) chloride / tetrahydrofuran / -10 °C / Reflux 2: hydrazine hydrate / ethanol / 2 h / Reflux 3: benzene / 1 h / 20 °C
  • 13
  • [ 425645-31-4 ]
  • [ 1352548-24-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium tetrahydroborate; aluminum (III) chloride / tetrahydrofuran / -10 °C / Reflux 2: hydrazine hydrate / ethanol / 2 h / Reflux 3: pyridine / 12 h / 0 - 20 °C 4: perchloric acid; acetic acid / water / Reflux
  • 14
  • [ 425645-31-4 ]
  • [ 1352548-24-3 ]
  • [ 1352548-33-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium tetrahydroborate; aluminum (III) chloride / tetrahydrofuran / -10 °C / Reflux 2: hydrazine hydrate / ethanol / 2 h / Reflux 3: pyridine / 12 h / 0 - 20 °C 4: hydrogenchloride; water / ethanol / 6 h / Reflux
  • 15
  • [ 425645-31-4 ]
  • [ 1352548-31-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: piperidine / ethanol / 0.08 h / Reflux 2.1: sodium tetrahydroborate / ethanol / 0.17 h / Reflux 2.2: pH 7 / Cooling 3.1: hydrogenchloride; water; acetic acid / 0.67 h / Reflux 3.2: 0.5 h / Reflux 3.3: 20 °C 4.1: potassium hydroxide / dimethyl sulfoxide / 0.33 h / 20 °C 5.1: hydrazine hydrate / ethanol / 2 h / Reflux 6.1: pyridine / 12 h / 0 - 20 °C 7.1: perchloric acid; water; acetic acid / Reflux
  • 16
  • [ 425645-31-4 ]
  • [ 1352548-32-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium tetrahydroborate; aluminum (III) chloride / tetrahydrofuran / -10 °C / Reflux 2: hydrazine hydrate / ethanol / 2 h / Reflux 3: pyridine / 12 h / 0 - 20 °C 4: perchloric acid; acetic acid / water / Reflux
  • 17
  • [ 425645-31-4 ]
  • [ 2033-24-1 ]
  • [ 1266525-99-8 ]
YieldReaction ConditionsOperation in experiment
86% With piperidine In ethanol for 0.0833333h; Reflux; 6.1. General procedure for synthesis of compounds 17a,b. General procedure: Mixture of aldehyde 16 (43.3 mmol) and Meldrum's acid (9.3 g, 64.9 mmol) in ethanol (100 mL) was heated until full dissolution of reagents. Then a drop of piperidine was added. The reaction mixture was refluxed for 5 min and cooled to room temperature. The formed precipitate was filtered off and recrystallized from acetone affording products 17.
  • 18
  • [ 425645-31-4 ]
  • [ 2033-24-1 ]
  • [ 1352548-39-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: piperidine / ethanol / 0.08 h / Reflux 2.1: sodium tetrahydroborate / ethanol / 0.17 h / Reflux 2.2: pH 7 / Cooling
  • 19
  • [ 425645-31-4 ]
  • [ 29431-37-6 ]
  • [ 109-77-3 ]
  • 7-amino-5-[5-(4-methyl-2-nitrophenyl)-2-furyl]-3,4-dihydro-1H-isothiochromene-6,8-dicarbonitrile 2,2-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With piperidine In ethanol for 5h; Reflux; regioselective reaction;
  • 20
  • [ 425645-31-4 ]
  • 2-[4-(N,N-dimethylamino)phenyl]pyrrolidine [ No CAS ]
  • N,N-dimethyl-4-(1-((5-(4-methyl-2-nitrophenyl)furan-2-yl)methyl)pyrrolidin-2-yl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
87.1% With sodium tris(acetoxy)borohydride; glacial acetic acid In 1,2-dichloro-ethane at 20℃; for 4h; Inert atmosphere; 4.2.22 N,N-dimethyl-4-(1-((5-(4-methyl-2-nitrophenyl)furan-2-yl)methyl)pyrrolidin-2-yl)aniline (14a) General procedure: 5-(4-methyl-2-nitrophenyl)furan-2-carbaldehyde (30mg, 130μmol) and N,N-dimethyl-4-(pyrrolidin-2-yl)aniline (30mg, 156μmol) were mixed in 1,2-dichloroethane (2mL) followed by the addition of acetic acid (23.5mg, 391μmol) and NaBH(OAc)3 (83mg, 391μmol). The mixture was stirred at room temperature for 4h. The mixture was quenched with saturated sodium bicarbonate solution and extracted with dichloromethane three times. The combined organic phase was dried over anhydrous Na2SO4 and concentrated to give a crude product, which was purified by silica gel column chromatography to get 46mg, yield: 87.1%.
87.1% With sodium tris(acetoxy)borohydride; glacial acetic acid In 1,2-dichloro-ethane at 20℃; for 4h; Inert atmosphere; 4.2.22 N,N-dimethyl-4-(1-((5-(4-methyl-2-nitrophenyl)furan-2-yl)methyl)pyrrolidin-2-yl)aniline (14a) General procedure: 5-(4-methyl-2-nitrophenyl)furan-2-carbaldehyde (30mg, 130μmol) and N,N-dimethyl-4-(pyrrolidin-2-yl)aniline (30mg, 156μmol) were mixed in 1,2-dichloroethane (2mL) followed by the addition of acetic acid (23.5mg, 391μmol) and NaBH(OAc)3 (83mg, 391μmol). The mixture was stirred at room temperature for 4h. The mixture was quenched with saturated sodium bicarbonate solution and extracted with dichloromethane three times. The combined organic phase was dried over anhydrous Na2SO4 and concentrated to give a crude product, which was purified by silica gel column chromatography to get 46mg, yield: 87.1%.
  • 21
  • [ 27329-70-0 ]
  • [ 5326-34-1 ]
  • [ 425645-31-4 ]
YieldReaction ConditionsOperation in experiment
38.3% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium carbonate In ethylene glycol dimethyl ether; ethanol; lithium hydroxide monohydrate for 8h; Inert atmosphere; Reflux; 4.2.21 5-(4-methyl-2-nitrophenyl)furan-2-carbaldehyde (13a) General procedure: 1-bromo-4-methyl-2-nitrobenzene (200mg, 926μmol) and (5-formylfuran-2-yl)boronic acid (155mg, 1.11mmol) were mixed in 2mL dimethoxyethane, 1mL ethanol and 1mL water followed by the addition of Pd(PPh3)2Cl2 (65mg, 92.6μmol) and K2CO3 (256mg, 1.85mmol). The mixture was heated at reflux under the protection of nitrogen for 8h and then cooled to room temperature. The mixture was diluted with water and extracted with ethyl acetate three times. The combined organic phase was dried over anhydrous Na2SO4 and concentrated to give a crude product, which was purified by silica gel column chromatography to get 82mg, yield: 38.3%.
38.3% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium carbonate In ethylene glycol dimethyl ether; ethanol; lithium hydroxide monohydrate for 8h; Inert atmosphere; Reflux; 4.2.21 5-(4-methyl-2-nitrophenyl)furan-2-carbaldehyde (13a) General procedure: 1-bromo-4-methyl-2-nitrobenzene (200mg, 926μmol) and (5-formylfuran-2-yl)boronic acid (155mg, 1.11mmol) were mixed in 2mL dimethoxyethane, 1mL ethanol and 1mL water followed by the addition of Pd(PPh3)2Cl2 (65mg, 92.6μmol) and K2CO3 (256mg, 1.85mmol). The mixture was heated at reflux under the protection of nitrogen for 8h and then cooled to room temperature. The mixture was diluted with water and extracted with ethyl acetate three times. The combined organic phase was dried over anhydrous Na2SO4 and concentrated to give a crude product, which was purified by silica gel column chromatography to get 82mg, yield: 38.3%.
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