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Chemical Structure| 15121-84-3 Chemical Structure| 15121-84-3

Structure of 15121-84-3

Chemical Structure| 15121-84-3

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Product Details of [ 15121-84-3 ]

CAS No. :15121-84-3
Formula : C8H9NO3
M.W : 167.16
SMILES Code : O=[N+](C1=CC=CC=C1CCO)[O-]
MDL No. :MFCD00007192
InChI Key :SLRIOXRBAPBGEI-UHFFFAOYSA-N
Pubchem ID :27054

Safety of [ 15121-84-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 15121-84-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.25
Num. rotatable bonds 3
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 46.2
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

66.05 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.36
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.36
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.13
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.49
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.16
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.04

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.91
Solubility 2.08 mg/ml ; 0.0124 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.35
Solubility 0.748 mg/ml ; 0.00447 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.0
Solubility 1.65 mg/ml ; 0.00989 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.35 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

2.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.78

Application In Synthesis of [ 15121-84-3 ]

* 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 [ 15121-84-3 ]

[ 15121-84-3 ] Synthesis Path-Downstream   1~36

  • 1
  • [ 15121-84-3 ]
  • [ 5339-85-5 ]
YieldReaction ConditionsOperation in experiment
100% EXAMPLE 5 The same procedure of Example 1 was repeated, except for increasing the amount of sodium hydroxide to 0.06 g (0.0015 mol). When uptake of hydrogen ceased in 43 minutes, the reaction was complete. The reaction mixture was cooled and allowed to stand. The supernatant liquor was recovered by decantation and analyzed by gas chromatography. As a result, the conversion of 2-(o-nitrophenyl)ethanol was 100percent and the yield of 2-(o-aminophenyl)ethanol was 99.5percent.
100% EXAMPLE 6 The same procedure of Example 5 was repeated, except for using the catalyst spent in Example 5. The reaction was complete in 74 minutes when uptake of hydrogen ceased. As a result of gas chromatography of the reaction mixture, the conversion of 2-(o-nitrophenyl)ethanol was 100percent, and the yield of 2-(o-aminophenyl)ethanol was 99.2percent.
100% As a result, the conversion of 2-(o-nitrophenyl)ethanol was 100percent, and the yield of 2-(o-aminophenyl)ethanol was 98.7percent.
47.0% aluminum nickel; COMPARATIVE EXAMPLE 2 The procedure of Comparative Example 1 was repeated, except for using the Raney nickel catalyst spent in Comparative Example 1. The reaction required 300 minutes for completion. As a result of gas chromatography of the reaction mixture, the conversion of 2-(o-nitrophenyl)ethanol was 47.0percent and the yield of 2-(o-aminophenyl)ethanol was 42.6percent.
00% EXAMPLE 2 The same procedure of Example 1 was repeated, except for increasing the amount of sodium hydroxide to 0.09 g (0.0023 mol). After 20 minutes' reaction, no uptake of hydrogen was observed, and the resulting reaction mixture was analyzed by gas chromatography. As a result, the conversion of 2-(o-nitrophenyl)ethanol was 00percent, and the yield of 2-(o-aminophenyl)ethanol was 98.9percent.
With potassium hydroxide; EXAMPLE 4 The same procedure of Example 1 was repeated, except for replacing sodium hydroxide with 0.09 g (0.0016 mol) of potassium hydroxide. When uptake of hydrogen ceased in 33 minutes, the reaction was stopped. Gas chromatography of the reaction mixture revealed that the conversion of 2-(o-nitrophenyl)ethanol and the yield of 2-(o-aminophenyl)ethanol were 100percent and 98.5percent, respectively.

  • 2
  • [ 15121-84-3 ]
  • [ 98-88-4 ]
  • [ 88057-18-5 ]
  • 4
  • [ 50-00-0 ]
  • [ 88-72-2 ]
  • [ 15121-84-3 ]
YieldReaction ConditionsOperation in experiment
25% With sodium hydroxide; In dimethyl sulfoxide; at 50℃; for 2h; Example54 N- (5- ( (4- (1, 2-dihydropyrrolo [3, 2, 1-hi] indol-5-yl) pyrimidin-2-yl) amino) -2- ( (2- (dimethylamino) ethyl) (methyl) amino) -6-methoxypyridin-3-yl) acrylamide (54) 2- (2-nitrophenyl) ethanol (54a) A mixture of 1-methyl-2-nitrobenzene (48 g, 0.35 mol) , Formaldehyde (10.4 g, 0.35 mol) , 20NaOH (3.6 ml) and DMSO was heated at 50 for 2 h. Then the mixture was cooled to r.t., diluted with water (200 mL) and extracted with Ethyl acetate (300 mL × 3) . The organic layers were combined and washed with water (200 mL × 2) and brine (200 mL) , dried over Na2SO4. The solids were filtered out and the filtrate was concentrated in vacuum. The crude product was purified by column chromatography on silica gel eluting with ethyl acetate/petroleum ether (1:1) to give 2- (2-nitrophenyl) ethanol (54a) as brown oil (14.4 g, 25).
  • 5
  • [ 15121-84-3 ]
  • [ 16793-89-8 ]
YieldReaction ConditionsOperation in experiment
81% With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0℃; for 0.75h; 1-(2-bromoethyl)-2-nitrobenzene; Triphenylphosphine (6.60 g, 25.2 mmol) was dissolved in dichloromethane (75 ml). Mixture was cooled to 0° C. 2-Nitrophenethyl alcohol (3.0 ml, 21.36 mmol) was added to the mixture drop-wise. A solution of carbon tetrabromide (8.50 g, 25.6 mmol) in 5 mL dichloromethane was added to the reaction mixture drop-wise. Reaction stirred at 0° C. for 45 minutes. Mixture was concentrated by roto-vap. Residue was treated with 100 mL diethyl ether. Solids were filtered off, washed with diethyl ether and discarded. Filtrate was concentrated. Silica gel chromatography on the residue eluting ethyl acetate-hexanes afforded the title compound as yellow oil in 81percent yield. 1H NMR (300 MHz, CHLOROFORM-D) delta ppm 7.97 (d, J=8.05 Hz, 1 H) 7.49-7.68 (m, 1 H) 7.41 (t, J=7.68 Hz, 2 H) 3.66 (t, J=6.77 Hz, 2 H) 3.43 (t, J=7.14 Hz, 2 H).
With phosphorus tribromide; In water; benzene; (1) Preparation of 2-(2-nitrophenyl)ethyl bromide 2.5 ml of <strong>[15121-84-3]2-(2-nitrophenyl)ethanol</strong> and 5.4 ml of PBr3 were stirred and mixed at 0° C. for 30 minutes to carry out reaction, and the resultant reaction mixture was diluted with 30 ml of benzene and the diluted mixture was then poured into 30 ml of water. The separated organic layer was separated, dried over anhydrous sodium sulfate, and then treated under reduced pressure to distill off the solvent, thereby obtaining 3 g of the crude product of 2-(2-nitrophenyl)ethyl bromide.
With phosphorus tribromide; In water; (1) Preparation of 2-(2-nitrophenyl)ethyl bromide (compound 11): First, 2.5 ml of <strong>[15121-84-3]2-(2-nitrophenyl)ethanol</strong> and 5.4 ml of PBr3 were mixed and stirred at 0° C. for 30 minutes to perform reaction therebetween, and the resulting reaction mixture was diluted with 30 ml of benzene and was then poured into 30 ml of water. Afterward, the separated organic layer was collected, dried over anhydrous sodium sulfate, and then treated under reduced pressure to distill off the solvent therefrom, thereby preparing 3 g of a crude product, 2-(2-nitrophenyl)ethyl bromide (compound 11).
With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0℃; Triphenylphosphine (39.2 g, 0.150 mol) and carbon tetrabromide (49.5 g, 0.150 mol) were added sequentially to a solution of 2-(2-hydroxyethyl)-nitrobenzene (25.0 g, 0.150 mol) in methylene chloride (400 mL) at 0OC. The reaction was stirred overnight and quenched with saturated sodium bicarbonate solution. The methylene chloride phase was washed with saturated brine and dried over magnesium sulfate. The crude product was treated with ethyl acetate, and the precipitated triphenylphosphine oxide removed by filtration. Further purification by flash chromatography by (silica gel, 0-10percent ethyl acetate in hexane gradient elution) produced the title compound (27.9 g).
With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20℃; 1-(2-Bromoethyl)-2-nitrobenzene; To a solution of 1-(2-hydroxyethyl)-2-nitrobenzene (21 ml, 150 mmol) and triphenylphosphine (39.2 g, 150 mmol) in DCM (400 ml) at 0° C. was add CBr4 (49.5 g, 150 mmol) in portions and the reaction mixture was stirred from 0° C. to RT overnight. The reaction mixture was quenched with sat. aq. Na2CO3, the layers were separated and the organic layer was washed with brine, dried (MgSO4) and evaporated to dryness. The residue was treated with EtOAc and the precipitated Ph3O was filtered and the solvent removed. This was repeated twice more. Purification by column chromatography (0percent to 10percent EtOAc in Hx) gave an oil that solidified on standing.
With carbon tetrabromide; triphenylphosphine; In dichloromethane; INTERMEDIATE 7 3 -f 4-PiperidinyD- 1 ,3 A5-tetrahydro-2H- 1 ,3 -benzodiazapin-2-one hydrochloride Step A. 2-(2-Bromoetfayl)nitrobenzene; Triphenylphosphine (39.2 g, 0.150 mol) and carbon tetrabromide (49.5 g, 0.150 mol) were added sequentially to a solution of 2-(2-hydroxyethyl)-nitrobenzene (25.0 g, 0.150 mol) in methylene chloride (400 mL) at O0C. The reaction was stirred overnight and quenched EPO <DP n="71"/>with saturated sodium bicarbonate solution. The methylene chloride phase was washed with saturated brine and dried over magnesium sulfate. The crude product was treated with ethyl acetate, and the precipitated triphenylphosphine oxide removed by filtration. Further purification by flash chromatography by (silica gel, 0-10percent ethyl acetate in hexane gradient elution) produced the title compound (27.9 g).
With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0℃; Triphenylphosphine (39.2 g, 0.150 mol) and carbon tetrabromide (49.5 g, 0.150 mol) were added sequentially to a solution of 2-(2-hydroxyethyl)-nitrobenzene (25.0 g, 0.150 mol) in methylene chloride (400 mL) at O0C. The reaction was stirred overnight and quenched with saturated sodium bicarbonate solution. The methylene chloride phase was washed with saturated brine and dried over magnesium sulfate. The crude product was treated with ethyl acetate, and the precipitated triphenylphosphine oxide removed by filtration. Further purification by flash chromatography by (silica gel, 0-10percent ethyl acetate in hexane gradient elution) produced the title compound (27.9 g).
With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0℃; (i) Triphenylphosphine (2.62 g, 10.0 mmol) and carbon tetrabromide (3.32 g, 10.0 mmol) were added sequentially to a solution of 2-(2-hydroxyethyl)-nitrobenzene(1.41 ml, 10.0 mmol) in dichloromethane (50 ml) at O0C. The reaction was stirred overnight and quenched with saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over anhydrous magnesium sulphate and concentrated in vacuo. The residue was treated with ethyl acetate, and the precipitated triphenylphosphine oxide removed by filtration. Purified by flash-silica gel column chromatography, eluting with a 0-100percent gradient of ethyl acetate in hexane to yield 2-(2-Bromoethyl)-nitrobenzene (2.30 g).

  • 6
  • [ 31912-02-4 ]
  • [ 15121-84-3 ]
  • 8
  • [ 39830-70-1 ]
  • [ 15121-84-3 ]
  • 9
  • [ 201230-82-2 ]
  • [ 15121-84-3 ]
  • 4,5-dihydro-3,1-benzoxazepin-2(1H)-one [ No CAS ]
  • 9,14,17,18-Tetrahydro-5H,8H-7,16-dioxa-5,14-diaza-dibenzo[a,h]cyclotetradecene-6,15-dione [ No CAS ]
  • 10
  • [ 15121-84-3 ]
  • 3-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1H-pyridin-2-one [ No CAS ]
  • 3-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-[2-(2-nitro-phenyl)-ethoxy]-pyridine [ No CAS ]
  • 11
  • [ 15121-84-3 ]
  • [ 1054607-95-2 ]
  • 3-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-[2-(2-nitro-phenyl)-ethoxy]-quinoline [ No CAS ]
  • 12
  • [ 15121-84-3 ]
  • [1,2,4]Triazol-1-yl-phosphonic acid 2-chloro-phenyl ester (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester [ No CAS ]
  • (5'-O-Tritylthymidin-3')(2-chlorphenyl)(2-nitrophenylaethyl)phosphorsaeureester [ No CAS ]
  • 13
  • [ 15121-84-3 ]
  • [1,2,4]Triazol-1-yl-phosphonic acid 2,5-dichloro-phenyl ester (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester [ No CAS ]
  • [ 74706-80-2 ]
  • 14
  • [ 15121-84-3 ]
  • [ 120-72-9 ]
YieldReaction ConditionsOperation in experiment
100% Pd-C; REFERENTIAL EXAMPLE 2 The procedures of Referential Example 1 were repeated except that the catalyst and the reaction time were changed to 0.59 g of 5% Pd-C of Nippon Engelhard Ltd. and 1.5 hours. The conversion of 2-(o-nitrophenyl)ethanol was 100% and the yield of indole was 39.2%.
92% With C28H28ClNO2Ru; oxygen; potassium carbonate; In isopropyl alcohol; at 130℃; for 6h; Application Example 1 : In an air atmosphere (presence of oxygen), placed in a magnetic Teflon tube in a high pressure reactor, ruthenium added as shown in formula (A2) of the complex structure of 5mg (0.01mmol, 3mol% equivalent of catalyst ), 0.3mmol 2- (2- nitrophenyl) ethanol, 3ml isopropanol and 0.3mmol of potassium carbonate, stirred at 130 6 hours. After completion of the reaction, the solvent was removed using a rotary evaporator, transferred to a separatory funnel and extracted with diethyl ether and water were added, the organic layers were combined, column chromatography to give indole (32 mg of, 92% yield).
  • 15
  • [ 15121-84-3 ]
  • [ 579-71-5 ]
  • 16
  • [ 15121-84-3 ]
  • [ 53676-18-9 ]
  • [ 7791-71-1 ]
  • [ 74706-80-2 ]
  • 17
  • [ 15121-84-3 ]
  • [ 2937-50-0 ]
  • [ 149913-86-0 ]
  • [ 149913-90-6 ]
  • 20
  • [ 15121-84-3 ]
  • [ 98-59-9 ]
  • [ 69628-96-2 ]
YieldReaction ConditionsOperation in experiment
92% 2-Nitrophenethyl alcohol (15 g, 89.7 mmol) was dissolved in 450 mL methylene chloride. Triethylamine (37.5 mL, 269 mmol) was added over 10 min and the reaction mixture was stirred at 0° C. for 1 hour (h). Tosyl chloride (20.52 g, 110 mmol) was added slowly to the mixture at 0° C. The reaction was stirred at room temperature (rt) overnight and was concentrated. The residue was dissolved in methylene chloride and washed with water, 1 N hydrochloric acid (HCl), then water. The organic layer was dried over sodium sulfate and evaporated. The residue was triturated with hexanes and 26.44 grams (g) of off-white crystals were collected. Yield 92percent; 1H NMR (400 MHz, CDCl3) delta 7.93 (d, J=9.7 Hz, 1H), 7.91 (d, J=9.7 Hz, 2H), 7.64 (t, 1H), 7.39 (m, 2H), 7.24 (s, 2H), 4.32 (t, J=6 Hz, 2H), 3.24 (t, J=6 Hz, 2H), 2.41 (s, 3H).
  • 21
  • [ 15121-84-3 ]
  • [ 77-78-1 ]
  • [ 102871-91-0 ]
  • 24
  • [ 15121-84-3 ]
  • [ 1969-73-9 ]
YieldReaction ConditionsOperation in experiment
51% With Dess-Martin periodane; In dichloromethane; at 20℃;Inert atmosphere; Into a 500-L 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-(2-nitrophenyl)ethan-1 -ol (300 g, 1.79 mol, 1.00 equiv) in dichloromethane (3000 ml_), Dess-Martin (837.8 g, 1 .10 equiv). The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 2 L of water/ice. The pH value of the solution was adjusted to 8 with sodium carbonate. The resulting solution was extracted with 3x2 L of dichloromethane and the organic layers combined. The resulting mixture was washed with 3x1 L of sodium chloride. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :1 ). This resulted in 150 g (51 %) of 2-(2- nitrophenyl)acetaldehyde as yellow oil.
  • 25
  • [ 15121-84-3 ]
  • [ 108-24-7 ]
  • [ 833-43-2 ]
  • 26
  • [ 75-44-5 ]
  • [ 15121-84-3 ]
  • [ 179691-21-5 ]
YieldReaction ConditionsOperation in experiment
94% In tetrahydrofuran; b 2-(2-nitrophenyl)ethoxycarbonyl chloride Phosgene was introduced into a solution of <strong>[15121-84-3]2-(2-nitrophenyl)ethanol</strong> (5.2 g, 31 mmol) in THF (20 ml, dist. over CaH2) at room temperature under stirring. After 1.5 h, the excess phosgene and the solvent were removed by distillation in a high vacuum. 2-(2-nitrophenyl)ethoxycarbonyl chloride (6.69 g, 94%) was obtained as a yellow oil. Rf (SiO2, CHCl3) 0.84 UV(CH3 CN), lambdamax [nm] (log epsilon): 202 (4.12), 218 (shoulder, 3.74); 256 (3.70); 298 (shoulder, 3.16); 346 (shoulder, 2.59) 1 H-NMR (250 MHz, CDCl3): 7.99 (dd, H--C(3)); 7.48 (m, 3 arom. H); 4.62 (t, alpha-CH2); 3.31 (t, beta--CH2) Anal. calcd. for C9 H8 ClNO4 (229.62): C 47.08, H 3.51, N 6.10; found: C 47.30, H 3.70, N 6.00
  • 27
  • [ 15121-84-3 ]
  • [ 28917-41-1 ]
YieldReaction ConditionsOperation in experiment
With pyridine; thionyl chloride; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; chloroform; Example 1 2-(2-nitrophenyl)ethyl chloride 2.1 ml abs. pyridine and 21.62 g thionyl chloride (13.3 ml,. 0.18 mol) is added to 10.13 9 <strong>[15121-84-3]2-(2-nitrophenyl)ethanol</strong> (60 mmol) in 36 ml abs. toluene. After 2 h reflux, this is cooled and poured onto ice. The ice water is mixed with 50 ml chloroform and extracted 2* each with 50 ml chloroform. The combined organic phases are neutralized 2* each with 100 ml saturated bicarbonate solution. After drying with Na2 SO4, this is filtered and rotary evaporated. After distillation under high-vacuum, 9.7 9 (50 mmol,. 87percent) 2-(2-nitrophenyl)ethyl chloride is obtained as a yellow oil with a boiling point of 66 to 67° C. (0.001 mbar). TLC (silica gel): Rf =0.39 (PE/EE 9:1); 1 H-NMR (250 MHz, CDCl3): 8.00 (dd, 1H, arom. H, o to NO2), 7.59 (t, 1H, arom. H), 7.45 (m, 2H, arom. H), 3.85 (t, 2H, alpha-CH2), 3.38 (t, 2H, beta-CH2); UV (MeOH), lambda [nm] (1 g epsilon): 204 (4.06), [216 (3.78)], 256 (3.69).
  • 28
  • [ 15121-84-3 ]
  • [ 503-38-8 ]
  • [ 179691-21-5 ]
  • 30
  • [ 15121-84-3 ]
  • [ 75-36-5 ]
  • [ 833-43-2 ]
  • 31
  • [ 7697-37-2 ]
  • [ 103-45-7 ]
  • [ 100-27-6 ]
  • [ 15121-84-3 ]
YieldReaction ConditionsOperation in experiment
COMPARATIVE EXAMPLE 1 In a 300 ml-volume autoclave were charged 30 g (0.18 mol) of 2-(o-nitrophenyl)ethanol isolated and purified by distillation, 90 g of methanol, and 0.3 g of Raney nickel ("NDT-90", a trade name of Kawaken Fine Chemical Co., Ltd.). After displacing the atmosphere with hydrogen several times, the hydrogen pressure was elevated up to 5 kg/cm2 G. Then, the temperature was raised up to 80° C. while stirring at 1,000 rpm, at which the reaction started. The hydrogen was continuously fed to keep the pressure at 8.5 kg/cm2 G. It was 184 minutes until uptake of hydrogen ceased.
  • 35
  • [ 15121-84-3 ]
  • [ 7732-18-5 ]
  • zinc dust [ No CAS ]
  • calcium chloride [ No CAS ]
  • [ 5339-85-5 ]
  • 36
  • [ 15121-84-3 ]
  • ClCOX [ No CAS ]
  • [ 179691-21-5 ]
 

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