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[ CAS No. 10220-22-1 ]

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2D
Chemical Structure| 10220-22-1
Chemical Structure| 10220-22-1
Structure of 10220-22-1 *Storage: {[proInfo.prStorage]}

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Product Details of [ 10220-22-1 ]

CAS No. :10220-22-1MDL No. :MFCD00020819
Formula : C10H12N2O2 Boiling Point : 349.9°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :192.21Pubchem ID :352305
Synonyms :

Computed Properties of [ 10220-22-1 ]

TPSA : 49.1 H-Bond Acceptor Count : 3
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.40 Rotatable Bond Count : 1

Safety of [ 10220-22-1 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 10220-22-1 ]

  • Upstream synthesis route of [ 10220-22-1 ]
  • Downstream synthetic route of [ 10220-22-1 ]

[ 10220-22-1 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 10220-22-1 ]
  • [ 2632-65-7 ]
YieldReaction ConditionsOperation in experiment
85% With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 9 h; Inert atmosphere; Schlenk technique General procedure: The nitrophenyl analogue 7a–7e (7.5 mmol) was dissolved in ethanol (50 mL), and to this solution was added 10percent Pd/C (0.2 g). The reaction mixture was stirred at room temperature under an atmosphere of H2 for 9 h. After completion of the reaction, the resulting mixture was filtered through Celite. The filtrate was concentrated under high vacuum to afford the desired aniline derivatives 8a–8e.
80% With ammonium hydroxide; sodium dithionite In water for 0.25 h; Reflux General procedure: To a solution of 1-(substituted) 4-nitrobenzene IVa,b,e,f(0.01 mol) in NH4OH (20 mL, 30percent), a solution of sodium dithionite(7 g, 0.04 mol) in water (30 mL) was quickly added, the reactionmixture was refluxed for 15 min. After cooling, the crude productwas filtered, washed and crystallized from methylene chloride toyield target compounds Va,b,e,f. 4-(Pyrrolidin-1-yl) aniline Vb
Yield 80percent as yellow oil, (as reported)
[66]
.
55% With sodium hydroxide In ethanol; acetic acid; ethyl acetate 2)
4-(Pyrrolidin-1-yl)-phenylamine (8).
To a solution of 7 in ethanol (20 mL) was added 10 wt percent Pd on carbon (Degussa) (25 mg, 23 .box.mol).
Glacial acetic acid (2-3 drops) was added to the reaction.
The reaction was placed under a H2 atmosphere and stirred for 16 hours, after which the reaction mixture was filtered through a pad of celite.
The filtrate was evaporated, and the residue then dissolved in ethyl acetate (20 mL) and washed with 2N HCl (aq. 15 mL).
The aqueous phase was isolated and then basified by the addition of 2N NaOH (aq. 20 mL).
The aqueous layer was extracted with ethyl acetate (20 mL*2).
The ethyl acetate extracts were dried over anhydrous magnesium sulfate, filtered, and evaporated to give crude 8 as a yellow oil (642 mg, 55percent for 2 steps).
Reference: [1] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 7, p. 1863 - 1873
[2] Bioorganic Chemistry, 2014, vol. 57, p. 65 - 82
[3] Advanced Synthesis and Catalysis, 2018, vol. 360, # 11, p. 2131 - 2137
[4] Patent: US2005/49286, 2005, A1,
[5] Justus Liebigs Annalen der Chemie, 1955, vol. 596, p. 1,151
[6] Journal of the American Chemical Society, 1948, vol. 70, p. 2223,2228
[7] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, <1951> 166, 168, [8] Chem.Abstr., 1951, p. 10236
[9] European Journal of Organic Chemistry, 2009, # 14, p. 2243 - 2250
[10] Patent: WO2014/189466, 2014, A1, . Location in patent: Paragraph 000121-000122
[11] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 3057 - 3061
[12] Organic Letters, 2017, vol. 19, # 24, p. 6486 - 6489
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