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[ CAS No. 532-12-7 ]

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Chemical Structure| 532-12-7
Chemical Structure| 532-12-7
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Product Details of [ 532-12-7 ]

CAS No. :532-12-7 MDL No. :MFCD00052019
Formula : C9H10N2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :146.19 g/mol Pubchem ID :442649
Synonyms :

Safety of [ 532-12-7 ]

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 [ 532-12-7 ]

  • Downstream synthetic route of [ 532-12-7 ]

[ 532-12-7 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 532-12-7 ]
  • [ 563-41-7 ]
  • 4-amino-1-[3]pyridyl-butan-1-one semicarbazone; hydrochloride [ No CAS ]
  • 2
  • [ 532-12-7 ]
  • [ 59-88-1 ]
  • 4-amino-1-[3]pyridyl-butan-1-one-phenylhydrazone; hydrochloride [ No CAS ]
  • 3
  • [ 532-12-7 ]
  • [ 93-97-0 ]
  • <i>N</i>-(4-oxo-4-[3]pyridyl-butyl)-benzamide [ No CAS ]
  • 4
  • [ 532-12-7 ]
  • [ 93-97-0 ]
  • 1-benzoyl-5-[3]pyridyl-2,3-dihydro-pyrrole [ No CAS ]
  • 6
  • [ 532-12-7 ]
  • <i>N</i>-(4-oxo-4-[3]pyridyl-butyl)-benzamide [ No CAS ]
  • 7
  • [ 532-12-7 ]
  • 4-amino-1-[3]pyridyl-butan-1-one oxime ; hydrochloride [ No CAS ]
  • 8
  • [ 532-12-7 ]
  • [ 5746-86-1 ]
YieldReaction ConditionsOperation in experiment
84.7% With hydrogen;palladium 10% on activated carbon; In methanol; for 5h; D. Preparation of Nornicotine: Myosmine (32 g, 0.219 mol) was dissolved in 150 ml of methanol and hydrogenated at atmospheric pressure with 1.3 g of 10% palladium on carbon as catalyst. After 5 hours the mixture was filtered and the filtrate was concentrated to get a brown solid (32 g, 94.9% purity by GC). It was further purified by vacuum distillation at 0.1 mm Hg to get pure nornicotine (27.46 g, 84.7% yield, 97.5% purity by GC). 1H NMR (CDCl3): delta 1.66-2.72 (2H,m), 3.0 (2H,m), 4.13 (1H,t), 7.24 (1H,m), 7.69 (1H, dt), 8.46 (1H,dd), and 8.59 (1H,d). 13C-NMR (CDCl3): delta 148.4, 148.1, 140.16, 134.1, 123.3, 60.0, 46.8, 34.2, and 25.4. IR: 3291, 2960, 1641, 1578 Cm-1.
With palladium 10% on activated carbon; hydrogen; In ethanol; for 12h;Large scale; The total crude Myosamine (from above) was takenup in 16 E ethanol, and 250 grams of 10% palladium on carbon was added and then resulting mixture, was stirred under hydrogen atmosphere for 12 hours, then filtered using celite, and washed with ethanol. The ethanol was removed using vacuum to give a dark brown non-viscous oil
The total crude Myosamine (from above) was taken up in 16 L methanol and 4 L of acetic acid, and the resulting solution was cooled to an internal temperature of -40 degrees centigrade, then 700 grams of sodium borohydride (granular) was added in portions over 1 hout The reaction was let warm to room temperature with stirring, and then submitted to vacuum distillation to remove most of the solvent. The resulting liquor was added 25 L of watet This was brought to pH>10 with NaOH. This was extracted three times with 15 L of dichloromethane, and the combined extracts were submitted to medium vacuum distillation to give a crude non-viscous dark brown colored oil.
With sodium tetrahydroborate; acetic acid; In methanol; at 20℃;Cooling with ice; General procedure: To a solution of substituted benzoic acid 3a-h (0.07 mol) inabsolute ethyl alcohol (100 mL) was slowly added thionyl chloride (15 mL). The mixture was heated to reflux for 2 h, and then cooledto room temperature. The solvent was removed and the solid residuewas dissolved in ethyl acetate (100 mL), and washed withsaturated NaHCO3 solution (100 mL 2). The organic layer wasdried and concentrated to give the intermediates 4a-h as paleyellow oily matter in 94.4e99.4% yield. They were used in the nextstep without additional purification.To a solution of NaH (5.6 g, 0.14 mol, 60%) in anhydrous THF(250 mL) was added 4a-h (0.07 mol) under the mechanical agitation.After heating to 60 C, N-Vinylpyrrolidone (0.07 mol) wasadded by dropwise and the mixture was heated to 72 C for 3 h.Then the reaction mixture was cooled to room temperature, thenpoured into ice water (500 mL), extracted with ethyl acetate(100 3 mL), and washed with saturated NH4Cl solution (300 mL)and brine (300 mL). The organic layer was dried and concentratedto give the intermediates 5a-h as brown oily matter in 82.3e94.2%yield, which was used in the next step without additionalpurification.A solution of 5a-h (0.06 mol) in THF (15 mL) was added to the5 N HCl (60 mL) under reflux. After the reaction mixture wasrefluxed for 3e5 h, then the reaction mixture was cooled to roomtemperature and concentrated in vacuo to remove the solvent THF.The pH was adjusted to 11 with saturated NaOH solution, thenextracted with ethyl acetate (100 mL 3), and washed with brine(150 mL 2). The organic layer was dried and concentrated to givethe intermediates 6a-h as brown oily matter in 82.8e87.2% yield,which was used in the next step without additional purification.To a solution of 6a-h (0.05 mol) in methanol (80 mL) was addedacetic acid two drops, and then NaBH4 (3.8 g, 0.1mol) was addedslowly under the condition of ice salt bath. After reaction at roomtemperature for 3 h, the solvent was removed and the residue wasdissolved in water. The pH was adjusted to 1 with 6 N HCl, washedwith methyl tertiary butyl ether (50 mL 3), and then the pH wasadjusted to 12 with NaOH solution. The mixturewas extracted withdichloromethane (100 mL 3), and washed with brine(150 mL 2). The organic layer was dried and concentrated to givethe brown oil, which was dissolved in acetone to form oxalic acidsalt. Intermediates 7a-h were obtained as white solid in42.3e55.6% yield.
With palladium 10% on activated carbon; hydrogen; In ethanol; under 38002.6 Torr; for 12h;Large scale; A solution of N-vinyl pyrrolidinone (4.5kg) in 2.5Kg of toluene was added to 2.5 Kg of Sodium Hydride (60% dispersion in mineral oil) as a stirred suspension in 20L of toluene. The resulting mixture was stirred for about 15 minutes at room temperature. 5Kg of ethyl nicotinate in 10Kg of toluene was added to the resulting mixture in portions and by a constant slow stream of liquor (light golden color). The exothermic reaction was controlled at an internal temperature of about 60C by controlling the rate of addition of the ethyl nicotinate - toluene solution. After addition of about one third of the ethyl nicotinate, a green precipitate was formed. After addition was completed, the green heterogeneous mixture was heated to an internal temperature of about 85 C and maintained at this temperature for about 12 hours. The resulting solution was injected into a precooled solution of 30L of 4N HCI at 0C followed by vigorous stirring for about 5 minutes. The layers were separated, and the toluene layer was washed once with 2.5Kg of 4N HCI. 8L of concentrated HCI was added to the combined acidic aqueous layers, and the reaction mixture was heated to boiling and maintained at this temperature for about 3 hours (or until the reaction was completed, as determined by thin layer chromatography (TLC)). The reaction mixture was cooled to 0C, and then neutralized with 50% sodium hydroxide solution while not allowing the internal temperature to go above 35 to 40 degrees centigrade. The pH was made very basic by addition of a sodium hydroxide solution (50%) until the pH reached 1 1 to 13 (as indicated by a blue color change on litmus paper). The resulting solution was extracted 4 times with 15L of dichloromethane, and the combined extracts were subjected to medium vacuum distillation to yield myosamine as a non-viscous brownish oil. (0138) [0081] 40L of anhydrous ethanol was added to the crude myosamine product, and the resulting solution was added to 2Kg of 10% palladium-on-carbon. The resulting mixture was subjected to hydrogen pressure of 50 atm. The reaction was completed within 12 hours. The resulting heterogeneous mixture was filtered through celite, and then washed twice with 10L of ethanol. The combined ethanolic solutions of the crude nornicotine product was subjected to vacuum distillation (29 inches Hg) at below 50C, and then the crude dark brown oil was taken up in 10L water. A solution of 5L of formaldehyde solution (37%) with 4L of formic acid (85%) was added to the resulting solution, and the mixture was heated to an internal temperature of 90 C and maintained at this temperature for 20 hours. The reaction mixture was cooled to -5 C, and then made basic (i.e., a pH greater than 10) by addition of a sodium hydroxide solution (50%). The basic liquor was then extracted 3 times with 15L of dichloromethane, and the combined extracts were subjected to med vacuum distillation to yield crude RS-Nicotine product as a dark brown oil. The dark brown oil was high vacuum distilled twice to yield RS-Nicotine having a purity that meets the requirements of the USP purity test.
With palladium 10% on activated carbon; hydrogen; In ethanol; under 19001.3 Torr; for 6h; Synthesis Example 1-R,S Nicotine Synthesis (0094) 1 equivalent of potassium hydride was added to a stirred solution of 1-vinyl-2-pyrrolidinone (2) in dry THF under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for about 20 minutes, then ethyl nicotinate (1 equivalent) was added and the resulting mixture was stirred for 24 hours at 65 degrees centigrade. The reaction was cooled and then acidified with 5% HCl, and then concentrated HCl was added and the resulting solution was refluxed for 48 hours. The pH was adjusted to 13 with sodium hydroxide, and the aqueous and organic layers of the resulting biphasic solution were separated three times using equal volumes of dichloromethane. The combined extracts from the separation were dried over sodium sulfate, filtered and the solvent evaporated to give an amorphous material. The amorphous material was taken up in 3 parts ethanol, and then palladium-on-carbon was added (about 10%) and the resulting mixture was subjected to hydrogen pressure for 6 hours (greater than 25 atmospheres). The resulting residue was diluted with more ethanol and filtered through celite. The solvent was evaporated to dryness under vacuum with minimal heat, and then the residue was taken up in a formic acid/formaldehyde solution (1:1). The resulting mixture was heated to an internal temperature of 90 degrees Celsius and maintained at this temperature over a period of 12 hours, and then cooled and neutralized with sodium hydroxide to a pH of greater than 10, and then extracted with dichloromethane and dried over sodium sulfate, filtered and concentrated to give a brown oil. This oil was vacuum distilled to give pure RS Nicotine.
With sodium tetrahydroborate; In isopropyl alcohol; at 20℃; 1.0 eq. of ethyl nicotinate, toluene, 1.6 eq. of sodium ethoxide, and 1.2 eq. of i-vinyl-2-pyrrolidone (NVP) were charged into a flask at room temperature of about 20C under anhydrous conditions. Then the reaction was run at 100C for 3 hours. The reaction was completed, and after the mixture had been cooled down to 30C, 695.0 g HCI (36% by weight in water) was added dropwise. The low boiling components like acetaldehyde, ethanol and the gaseous CO2 were removed by distillation, together with parts of the toluene and the water. When the reaction temperature reached 105C, distillation was stopped and the reaction mixture was stirred at a temperature between 100C and 105C overnight. After completion of the reaction, the pH was adjusted to a value between 9.5 to 10.5 using NaOH (30% by weight in water). 360.0 g iso propanol and 1.0 eq. of NaBH4 (in respect of the ethyl nicotinate) were charged into the reaction vessel. The reaction was run at room temperature (about 20C) for more than 3 hours (at this point the content of myosmine was below 3.0% by weight). 2.0 eq. of formic acid (HCOOH, in respect of the ethyl nicotinate) and 1.2 eq. paraformaldehyde ((HCHO)n, in respect of the ethyl nicotinate) were added and the mixture was stirred at 65C for at least 3 hours. After the reaction was finished (at this point the content of myosmine was below 0.5% by weight), the pH of the mixture was adjusted to a value of 13 to 14 using NaOH (30% by weight in water). Water was added until all inorganic solids were dissolved. The mixture was extracted twice with toluene. The combined organic phases were concentrated to obtain the crude product. By distillation of the crude product, racemic nicotine was obtained as a colorless oil with a purity of 98.9% (yield was 66.0%) as sample 1.
With sodium tetrahydroborate; isopropyl alcohol; at 10℃; General procedure: Iso-propanol (29.0 g, as given in Table 1a) and 1.0 eq. of NaBH4 (in respect of the ethyl nicotinate) were charged in portions during 1 hour into the reaction vessel. The reaction was run at about 10C for more than 3 hours (at this point the content of myosmine was below 3.0% by weight).

  • 9
  • [ 614-18-6 ]
  • [ 2399-66-8 ]
  • [ 141-52-6 ]
  • [ 71-43-2 ]
  • [ 532-12-7 ]
  • 10
  • [ 614-18-6 ]
  • [ 2399-66-8 ]
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  • 11
  • [ 98953-15-2 ]
  • [ 532-12-7 ]
  • 12
  • [ 109700-79-0 ]
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  • 15
  • [ 54-11-5 ]
  • [ 1121-55-7 ]
  • [ 536-78-7 ]
  • [ 532-12-7 ]
  • [ 487-19-4 ]
  • 16
  • [ 532-12-7 ]
  • [ 77287-34-4 ]
  • [ 85324-02-3 ]
  • 17
  • [ 532-12-7 ]
  • [ 407-25-0 ]
  • (R)-(+)-N-Trifluoroacetyl-2-(3-pyridinyl)pyrrolidine [ No CAS ]
  • (S)-(-)-N-Trifluoroacetyl-2-(3-pyridinyl)pyrrolidine [ No CAS ]
  • 18
  • [ 532-12-7 ]
  • [ 2258-42-6 ]
  • [ 54-11-5 ]
  • [ 25162-00-9 ]
  • 19
  • [ 532-12-7 ]
  • [ 2258-42-6 ]
  • [ 38840-03-8 ]
  • (R)-(+)-N-Formylnornicotinel [ No CAS ]
  • 20
  • [ 532-12-7 ]
  • [ 75195-77-6 ]
  • 22
  • (4-Oxo-4-pyridin-3-yl-butyl)-carbamic acid tert-butyl ester [ No CAS ]
  • [ 532-12-7 ]
  • 24
  • [ 36740-10-0 ]
  • [ 532-12-7 ]
  • [ 5746-86-1 ]
  • 25
  • Isopropyl-[1-pyridin-3-yl-4-(2,2,5,5-tetramethyl-[1,2,5]azadisilolidin-1-yl)-but-(E)-ylidene]-amine [ No CAS ]
  • [ 532-12-7 ]
  • 26
  • [ 22083-74-5 ]
  • [ 532-12-7 ]
  • [ 525-74-6 ]
  • [ 487-19-4 ]
  • [ 15569-85-4 ]
  • 3-(1-Methyl-2,3-dihydro-1H-pyrrol-2-yl)-pyridine [ No CAS ]
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