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[ CAS No. 2199-45-3 ] {[proInfo.proName]}

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Chemical Structure| 2199-45-3
Chemical Structure| 2199-45-3
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Product Details of [ 2199-45-3 ]

CAS No. :2199-45-3 MDL No. :MFCD04112537
Formula : C9H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :NJUXFNQDUIJYPO-UHFFFAOYSA-N
M.W : 167.21 Pubchem ID :137478
Synonyms :

Calculated chemistry of [ 2199-45-3 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.44
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.81
TPSA : 42.09 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.26
Log Po/w (XLOGP3) : 2.03
Log Po/w (WLOGP) : 1.81
Log Po/w (MLOGP) : 1.02
Log Po/w (SILICOS-IT) : 2.5
Consensus Log Po/w : 1.92

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.27
Solubility : 0.906 mg/ml ; 0.00542 mol/l
Class : Soluble
Log S (Ali) : -2.54
Solubility : 0.48 mg/ml ; 0.00287 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.86
Solubility : 0.233 mg/ml ; 0.00139 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.13

Safety of [ 2199-45-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2199-45-3 ]

* 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 [ 2199-45-3 ]

[ 2199-45-3 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 110-91-8 ]
  • [ 2199-45-3 ]
  • [ 50-00-0 ]
  • 4,5-dimethyl-3-morpholinomethyl-pyrrole-2-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride
  • 2
  • [ 600-28-2 ]
  • [ 75-16-1 ]
  • [ 2199-45-3 ]
YieldReaction ConditionsOperation in experiment
With diethyl ether Behandeln der Reaktions-Loesung mit Chlorameisensaeure-aethylester;
  • 4
  • [ 2199-45-3 ]
  • [ 75-36-5 ]
  • [ 2386-32-5 ]
  • 5
  • [ 2199-45-3 ]
  • [ 600-28-2 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid
  • 7
  • [ 2199-45-3 ]
  • [ 4635-59-0 ]
  • [ 94478-17-8 ]
YieldReaction ConditionsOperation in experiment
55% With aluminium trichloride In nitromethane at 20℃; for 24h;
  • 8
  • [ 2199-45-3 ]
  • ethyl 3-chloro-4,5-dimethylpyrrole-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With chlorine In chloroform
  • 9
  • [ 100445-43-0 ]
  • [ 2199-45-3 ]
YieldReaction ConditionsOperation in experiment
92% at 200℃; for 1h;
  • 10
  • [ 2199-45-3 ]
  • [ 112-16-3 ]
  • [ 192182-57-3 ]
YieldReaction ConditionsOperation in experiment
31% With aluminium trichloride In nitrobenzene for 72h;
YieldReaction ConditionsOperation in experiment
With acetic acid; zinc
  • 12
  • [ 5408-04-8 ]
  • [ 2199-45-3 ]
  • [ 2199-46-4 ]
YieldReaction ConditionsOperation in experiment
With water; zinc
With acetic acid; zinc
  • 13
  • [ 2199-45-3 ]
  • [ 26018-26-8 ]
YieldReaction ConditionsOperation in experiment
81% With ammonium cerium (IV) nitrate In tetrachloromethane; water; acetic acid at 0℃; for 1h;
55% With ammonium cerium(IV) nitrate In methanol; water at 20℃; for 3h;
  • 14
  • [ 50708-35-5 ]
  • [ 500801-00-3 ]
  • [ 2199-45-3 ]
YieldReaction ConditionsOperation in experiment
67% With 2,2'-azobis(isobutyronitrile) In n-heptane; chlorobenzene Heating;
  • 15
  • [ 2199-45-3 ]
  • [ 71703-41-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 90 percent / SnCl4 / 0.75 h / 0 - 5 °C 2: 72 percent / POCl3, N,N-dimethylformamide / 40 h / 40 °C 3: 83 percent / aq. KOH, N,N-dimethylformamide / 0.2 h / 20 °C
  • 16
  • [ 2199-45-3 ]
  • [ 74306-53-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90 percent / SnCl4 / 0.75 h / 0 - 5 °C 2: POCl3, N,N-dimethylformamide / 6 h / 60 °C
  • 17
  • [ 2199-45-3 ]
  • [ 74306-53-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90 percent / SnCl4 / 0.75 h / 0 - 5 °C 2: POCl3, N,N-dimethylformamide / 6 h / 60 °C
  • 18
  • [ 2199-45-3 ]
  • [ 71703-38-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90 percent / SnCl4 / 0.75 h / 0 - 5 °C 2: 72 percent / POCl3, N,N-dimethylformamide / 40 h / 40 °C
  • 19
  • [ 2199-45-3 ]
  • [ 350252-63-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 55 percent / Ce(NH4)2(NO3)6 / methanol; H2O / 3 h / 20 °C 2: aq. KOH / methanol / Heating 3: 0.58 g / KOAc; NaOAc*3H2O / 160 °C
  • 20
  • [ 2199-45-3 ]
  • [ 350252-61-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 55 percent / Ce(NH4)2(NO3)6 / methanol; H2O / 3 h / 20 °C 2: aq. KOH / methanol / 6 h / Heating 3: 1.75 g / KOAc; NaOAc*3H2O / 0.17 h / 160 °C
  • 21
  • [ 2199-45-3 ]
  • 5-(3-ethyl-4-methyl-5-oxo-1,5-dihydro-pyrrol-2-ylidenemethyl)-4-methyl-1<i>H</i>-pyrrole-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 55 percent / Ce(NH4)2(NO3)6 / methanol; H2O / 3 h / 20 °C 2: aq. KOH / methanol / Heating
  • 22
  • [ 2199-45-3 ]
  • [ 350252-66-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 55 percent / Ce(NH4)2(NO3)6 / methanol; H2O / 3 h / 20 °C 2: aq. KOH / methanol / 6 h / Heating
  • 23
  • [ 2199-45-3 ]
  • 9-butanoyl-2,7-dimethyl-3-ethyl-10H-dipyrrin-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 55 percent / Ce(NH4)2(NO3)6 / methanol; H2O / 3 h / 20 °C 2: aq. KOH / methanol / Heating 3: 0.58 g / KOAc; NaOAc*3H2O / 160 °C 4: 53 percent / AlCl3 / CH2Cl2 / 20 °C
  • 24
  • [ 2199-45-3 ]
  • 9-butanoyl-2,3-diethyl-7-methyl-10H-dipyrrin-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 55 percent / Ce(NH4)2(NO3)6 / methanol; H2O / 3 h / 20 °C 2: aq. KOH / methanol / 6 h / Heating 3: 1.75 g / KOAc; NaOAc*3H2O / 0.17 h / 160 °C 4: 50 percent / AlCl3 / CH2Cl2 / 20 °C
  • 25
  • [ 2199-45-3 ]
  • 3-dodecanoyl-1,4,5-trimethylpyrrole-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 31 percent / AlCl3 / nitrobenzene / 72 h 2: (C4H9)4NBr, NaOH / diethyl ether; CH2Cl2 / 8 h / Ambient temperature 3: aq. KOH / ethanol / 1 h / Heating
  • 26
  • [ 2199-45-3 ]
  • [ 1027254-30-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 31 percent / AlCl3 / nitrobenzene / 72 h 2: (C4H9)4NBr, NaOH / diethyl ether; CH2Cl2 / 8 h / Ambient temperature
  • 27
  • [ 1679-40-9 ]
  • [ 2199-45-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 55 percent / EtONa / ethanol / 4 h / -10 °C 2: 3 percent / various solvent(s) / Heating; further solvents
  • 28
  • ethyl 2-azido-5-methylhexa-2,4-dienoate [ No CAS ]
  • [ 2199-45-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 43 percent / toluene / 2 h / Heating 2: 92 percent / 1 h / 200 °C
  • 29
  • [ 2199-45-3 ]
  • [ 94922-64-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 55 percent / AlCl3 / nitromethane / 24 h / 20 °C 2: 92 percent / silver nitrate / dimethylformamide; H2O / 2 h / 60 °C 3: 79 percent / KOH / H2O; ethanol / 1 h / Heating; nitrogen atmosphere 4: 92 percent / sodium acetate, potassium acetate / 180 - 200 °C / nitrogen atmosphere
  • 30
  • [ 2199-45-3 ]
  • cyclopropyl 2,3-dimethyl-5-carboxypyrrol-4-yl ketone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 55 percent / AlCl3 / nitromethane / 24 h / 20 °C 2: 3percent NaOH / methanol / 5 h / Heating
  • 31
  • [ 2199-45-3 ]
  • [ 94922-63-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 55 percent / AlCl3 / nitromethane / 24 h / 20 °C 2: 92 percent / silver nitrate / dimethylformamide; H2O / 2 h / 60 °C 3: 79 percent / KOH / H2O; ethanol / 1 h / Heating; nitrogen atmosphere
  • 32
  • [ 2199-45-3 ]
  • [ 94478-21-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 55 percent / AlCl3 / nitromethane / 24 h / 20 °C 2: 3percent NaOH / methanol / 5 h / Heating 3: 0.17 h / 200 °C / in vacuo
  • 33
  • [ 2199-45-3 ]
  • cyclopropyl 2,3-dimethyl-5-formylpyrrol-4-yl ketone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 55 percent / AlCl3 / nitromethane / 24 h / 20 °C 2: 3percent NaOH / methanol / 5 h / Heating 3: 0.17 h / 200 °C / in vacuo 4: 83 percent / POCl3 / 1 h
  • 34
  • [ 2199-45-3 ]
  • [ 94478-20-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 55 percent / AlCl3 / nitromethane / 24 h / 20 °C 2: 92 percent / silver nitrate / dimethylformamide; H2O / 2 h / 60 °C 3: 79 percent / KOH / H2O; ethanol / 1 h / Heating; nitrogen atmosphere 4: 92 percent / sodium acetate, potassium acetate / 180 - 200 °C / nitrogen atmosphere 5: 91 percent / pyridine / 2 h / 40 °C
  • 35
  • [ 2199-45-3 ]
  • [ 94478-16-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 55 percent / AlCl3 / nitromethane / 24 h / 20 °C 2: 92 percent / silver nitrate / dimethylformamide; H2O / 2 h / 60 °C
  • 36
  • [ 2199-45-3 ]
  • 2,3-dimethyl-4-(4-acetoxybutyryl)-5-formylpyrrole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 55 percent / AlCl3 / nitromethane / 24 h / 20 °C 2: 92 percent / silver nitrate / dimethylformamide; H2O / 2 h / 60 °C 3: 79 percent / KOH / H2O; ethanol / 1 h / Heating; nitrogen atmosphere 4: 92 percent / sodium acetate, potassium acetate / 180 - 200 °C / nitrogen atmosphere 5: 91 percent / pyridine / 2 h / 40 °C 6: 66 percent / POCl3 / 1 h / 40 °C
  • 37
  • [ 2199-45-3 ]
  • 2,3-dimethyl-4-(4-acetoxybutyryl)-5-(ethoxycarbonyl)pyrrole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 55 percent / AlCl3 / nitromethane / 24 h / 20 °C 2: 59 percent / sodium acetate / acetic acid / 0.25 h / Heating
  • 38
  • [ 2199-45-3 ]
  • [ 491-18-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: AlCl3; CS2 2: hydrazine hydrate; ethanolic sodium ethylate solution / 170 °C
  • 39
  • [ 2199-45-3 ]
  • (3-benzoyl-4,5-dimethyl-pyrrol-2-yl)-(3-benzoyl-4,5-dimethyl-pyrrol-2-ylidene)-methane; hydrobromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: AlCl3; CS2 2: ethanolic NaOH 3: 220 °C 4: diethyl ether / unter Einleiten von Chlorwasserstoff und Behandeln des erhaltenen Imid-hydrochlorids mit Eis 5: aqueous methanol. HBr
Multi-step reaction with 4 steps 1: AlCl3; CS2 2: ethanolic NaOH 3: 220 °C 4: aqueous methanol. HBr
  • 40
  • [ 143193-92-4 ]
  • [ 5408-04-8 ]
  • [ 2199-45-3 ]
YieldReaction ConditionsOperation in experiment
54% With acetic acid; zinc In 1,4-dioxane; water at 58 - 82℃; for 2h; 3 Process detail Step 1: Prepare aqueous IV-A solution: 619 g of IV-A dissolved in 1.5 L of water. Step 2: To a 22 L 3-neck round bottom flask, under nitrogen, equipped with a mechanical stirrer, thermocouple/heating mantle apparatus, and an addition funnel, charge 697 g of VI-A. Step 3: To the VI-A add 1.4 L of dioxane. Step 4: To the solution add 3.4 L of water. Step 5: To the solution add 763 g of acetic acid. Step 6: To the mixture add aqueous IV-a solution. Step 7: Heat the mixture to 58°-60° C. Step 8 : To the mixture add zinc (Note 1). Step 9: Stir the mixture at 80°-82° C and monitor the reaction completeness by HPLC (Notes 2 and 3). Step 10: Cool the mixture to 25°-28° C. Step 11: Extract the mixture with 5.0 L of tert-butyl methyl ether. Step 12: Filter the bi-layered mixture through ordinary Whatman filter paper (Note 4). Step 13: Separate the layers. Step 14: Wash the organic layer with 2.5 L of water. Step 15: Separate the layers. Step 16: Dry the organic layer over 500 g of magnesium sulfate (Note 5). Step 17: Remove the magnesium sulfate by filtration. Step 18: Concentrate the filtrate to a dark brown solid. Step 19: Dry the solid under vacuum at 40° C for 16 hours. [00661 Results Weight: 512 g Purity % (w/w) or % (AUC): 77% AUC (HPLC) Molar yield or area yield: 54% [0067] Analytical In process control HPLC: Zorbax SB Phenyl 4.6 x 250 mm i. d., 5 pm, 90% water/10% CH3CN/0. 1% TFA to 10% water over 15 minutes, flow rate = 1.0 mL/minute, 10 ZL injection, column temperature = 50° C, X = 214 nm. Sample preparation: 3 drops of reaction mixture dissolved in 1.0 mL of 1: 1 water/CH3CN. Retention Times Peak Assignment Retention Time Rel No. Retention Time 1 VI-A 8. 5 minutes 2 VII-A 11. 4 minutes 3 Multiple smaller uncharacterized peaks. [0068] Process Efficiency Maximum volume step-14 L (Step 11). Minimum volume step-9.0 L (Step 6). [0069] Notes Note 1: The zinc is added in 10-15% portions over 90 minutes. The addition of each portion is accompanied by a temperature increase of 7°-10° C. Before the next addition, the temperature is adjusted to 70° C with a cool water bath. Note 2: The mixture may or may not reflux at this temperature, but the reflux temperature is probably 82°- 85° C. Note 3: The reaction is generally complete after this 30 minute stir period. Note 4: The filtration time is dependent on the amount of inorganic precipitates and in some cases has required 60 minutes. Note 5: On scale, the drying agent could probably be replaced. by a solvent exchange into dichloroethane (the solvent for the next reaction).
With acetic acid; zinc In 1,4-dioxane; water at 80℃;
  • 41
  • [ 2199-45-3 ]
  • [ 2386-32-5 ]
YieldReaction ConditionsOperation in experiment
64% Process detail Step 1: Prepare saturated sodium chloride solution: 220 g of sodium chloride dissolved in 580 mL of water. Step 2: Prepare acetic anhydride/dichloromethane solution: 408 g of acetic anhydride dissolved in 220 mL of dichloromethane. Step 3: Prepare VII-A/dichloromethane solution: 223 g of VII-A dissolved in 1.1 L of dichloromethane. Step 4: Charge 1.0 kg of aluminum chloride to a 12 L 3- neck round bottom flask that is under a nitrogen atmosphere, and is equipped with a water cooled condensor, addition funnel, and thermocouple. Step 5: Add 880 mL of dicloromethane to the aluminum chloride. Step 6: Cool the aluminum chloride/dichloromethane suspension to 5 10 C with an ice water bath. Step 7 : Add acetic anhydride/dichloromethane solution to the aluminum chloride suspension (Note 1). Step 8: Stir the aluminum chloride/acetic anhydride complex for 30 minutes (Note 2). Step 9: Add VII-A/dichloromethane solution to aluminum chloride/acetic anhydride complex (Notes 3 and 4). Step 10: Fit the 12 L round bottom flask with a heating mantle. Step 11: Heat the reaction mixture at reflux (34-37 C) and monitor the consumption of VII-A by HPLC (Notes 5 and 6). Step 12: Cool the reaction mixture to 24-26 C with a cool water bath. Step 13: Transfer the black mixture to a 10 L carboy. Step 14: Charge 4.4 L of water to the 12 L vessel. Step 15: Cool the water to 5-10 C with an ice water bath. Step 16: Quench the VIII-A mixture into the water (Note 7). Step 17: Separate the layers (Note 8). Step 18: Wash the aqueous layer with 800 mL of dichloromethane. Step 19: Separate the layers. Step 20: Combine the organic layers. Step 21: Wash the combined organic layers with 800 mL of saturated sodium chloride. Step 22: Separate the layers. Step 23: Using rotary evaporation at reduced pressure, concentrate the organic layer to a black solid. [00711 Results Weight: 223 g Purity % (w/w) or % (AUC) : 80% AUC Molar yield or area yield: 64% corrected yield. l0072] Analytical Method (HPLC) -Zorbax SB Phenyl; 5 um, 4.6 mm i. d. x 250 mm length; 90% water/10% acetonitrile/0.1% trifluoroacetic acid to 90% acetonitrile over 15 minutes, run time = 20 minutes, injection volume = 10) ho, flow rate = 1.0 mL/minute, column temperature = 50 C, wavelength = 214 nm. Retention Times Peak No. Assignment Retention Time 1 VII-A 11.4 minutes 2 VIII-A 10. 6 minutes [0073] Process Efficiency Maximum volume step-8.2 L Minimum volume step-1.9 L [0074] Notes Note 1: The addition was carried out dropwise over 25- 30 minutes and the temperature was not allowed to increase above 27 C. Note 2: The mixture should be homogeneous and light green colored. Note 3: The addition was carried out dropwise over 25- 30 minutes and the temperature was not allowed to increase above 30 C. Note 4: The mixture will be homogeneous and black colored. Note 5: A reaction time of 1-2 hours is typical. Note 6: Sample preparation : 3 drops of reaction mixture dissolved in 1.0 mL of 50% aqueous acetonitrile. Method (HPLC): see under Analytical section. Note 7: The quench was carried out dropwise over-2 hours and the temperature was not allowed to increase above 27 C. Note 8: The bi-layered mixture will be black and the interface might not be clear. If the interface is not clear, then removal of the organic layer by weight or volume is necessary.
  • 42
  • [ 2199-45-3 ]
  • [ 78-84-2 ]
  • [ 25573-80-2 ]
YieldReaction ConditionsOperation in experiment
45% 44 2,3-Dimethyl-4-isobutyl-5-carbethoxy-pyrrole STR52 EXAMPLE 44 2,3-Dimethyl-4-isobutyl-5-carbethoxy-pyrrole STR52 As in Example 32 but using 2,3-dimethyl-5-carbethoxy-pyrrole and isobutyraldehyde, pouring the mixture into water after 3 hrs and extracting the product from the alkaline mixture with ether. It was distilled (70°, 1 * 10-4 mm) and crystallized from pentane as colourless prisms (45%), m.p. 109°-111°. Anal. Calc. for C13 H21 NO2: C, 69.92; H, 9.48; N, 6.27. Found: C, 70.23; H, 9.79; N, 6.27.
  • 43
  • [ 2199-45-3 ]
  • [ 111-71-7 ]
  • [ 25573-81-3 ]
YieldReaction ConditionsOperation in experiment
In pentane 45 2,3-Dimethyl-4-n-heptyl-5-carbethoxy-pyrrole EXAMPLE 45 2,3-Dimethyl-4-n-heptyl-5-carbethoxy-pyrrole Obtained as in Example 44 using 2,3-dimethyl-5-carbethoxy-pyrrole and n-heptaldehyde, the product (b.p. 100°, 1 * 10-3 mm) formed colourless crystals (47%) from pentane, m.p. 68°-69°. Anal. Calc. for C16 H27 NO2: C, 72.41, H, 10.26; N, 5.28. Found: C, 72.23; H, 10.27; N, 5.15.
  • 44
  • [ 2199-45-3 ]
  • [ 6303-21-5 ]
  • [ 123-38-6 ]
  • [ 35030-47-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogen iodide; acetic acid In water 68 2-Carbethoxy-3-n-propyl-4,5-dimethylpyrrole EXAMPLE 68 2-Carbethoxy-3-n-propyl-4,5-dimethylpyrrole Hydriodic acid (d 1.95, 10 ml) was slowly added to 10 ml of stirred and cooled acetic acid; hypophosphorous acid (50%, 2 ml) was then added. 2-Carbethoxy-4,5-dimethylpyrrole (0.004 mol) was added to the mixture at room temperature followed by propionaldehyde (0.008 mol). The solution was stirred 21/2 h at ca. 25° C. then poured into 200 ml of water. This was made alkaline with ammonia, extracted with ether, and the ether was evaporated to leave the crude product. This was an oil which solidified after distillation (1 * 10-4 mm). It was recrystallized from aqueous ethanol, then from ethanol m.p. 101°-104° C. (lit. 102° C), yield 40%. STR68
  • 45
  • [ 2199-45-3 ]
  • [ 112-54-9 ]
  • [ 25573-82-4 ]
YieldReaction ConditionsOperation in experiment
46 2,3-Dimethyl-4-n-dodecyl-5-carbethoxy-pyrrole EXAMPLE 46 2,3-Dimethyl-4-n-dodecyl-5-carbethoxy-pyrrole As in Example 32 but using 2,3-dimethyl-5-carbethoxy-pyrrole and laurylaldehyde and stirring for 3 hrs. It formed colourless prisms (35%), m.p. 70°-71°. Anal. Calc. for C21 H37 NO2: C, 75.17; H, 11.12; N, 4.18. Found: C, 75.08; H, 11.04; N, 4.30.
  • 46
  • [ 2199-45-3 ]
  • [ 123-63-7 ]
  • [ 34549-93-4 ]
YieldReaction ConditionsOperation in experiment
43 2,3-Dimethyl-4-ethyl-5-carbethoxy-pyrrole STR51 EXAMPLE 43 2,3-Dimethyl-4-ethyl-5-carbethoxy-pyrrole STR51 As in Example 32 but using 2,3-dimethyl-5-carbethoxy-pyrrole and paraldehyde. Colourless prisms (51%), m.p. 95°-97° (lit16) m.p. 97°). Anal. Calc. for C11 H17 NO2: C, 67.66; H, 8.78; N, 7.17. Found: C, 67.59; H, 8.49; N, 7.23.
  • 47
  • [ 2199-45-3 ]
  • [ 2199-46-4 ]
YieldReaction ConditionsOperation in experiment
34 The preparation of 2,3,4-trimethyl-5-carbethoxy-pyrrole STR42 EXAMPLE 34 The preparation of 2,3,4-trimethyl-5-carbethoxy-pyrrole STR42 As in Example 32 but using 2,3-dimethyl-5-carbethoxy-pyrrole4). It formed colourless needles (72%), m.p. 127°-129°. Anal. Found: C, 66.13; H, 8.41; N, 7.71.
  • 48
  • [ 22428-91-7 ]
  • [ 5408-04-8 ]
  • [ 2199-45-3 ]
YieldReaction ConditionsOperation in experiment
10.03 g With zinc In water for 1h; Reflux;
  • 49
  • [ 2199-45-3 ]
  • [ 4868-31-9 ]
  • 50
  • [ 2199-45-3 ]
  • 4,5-dimethyl-N-(prop-2-yn-1-yl)-1H-pyrrole-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium hydroxide monohydrate / water; methanol / 70 °C 2: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 6 h / 70 °C / Inert atmosphere
  • 51
  • [ 2199-45-3 ]
  • N-(3-(imidazo[1,2-a]pyrimidin-3-yl)prop-2-yn-1-yl)-4,5-dimethyl-1H-pyrrole-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: lithium hydroxide monohydrate / water; methanol / 70 °C 2: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 6 h / 70 °C / Inert atmosphere 3: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / N,N-dimethyl-formamide / 50 °C / Inert atmosphere
Same Skeleton Products
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[ 2199-45-3 ]

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Chemical Structure| 85057-78-9

[ 85057-78-9 ]

5-(Ethoxycarbonyl)-3,4-dimethyl-1H-pyrrole-2-carboxylic acid

Similarity: 0.97

Chemical Structure| 2199-46-4

[ 2199-46-4 ]

Ethyl 3,4,5-trimethyl-1H-pyrrole-2-carboxylate

Similarity: 0.97

Chemical Structure| 4391-99-5

[ 4391-99-5 ]

Ethyl 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxylate

Similarity: 0.97

Chemical Structure| 33317-03-2

[ 33317-03-2 ]

Methyl 4,5-dimethyl-1H-pyrrole-2-carboxylate

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Related Parent Nucleus of
[ 2199-45-3 ]

Pyrroles

Chemical Structure| 2199-44-2

[ 2199-44-2 ]

Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate

Similarity: 0.97

Chemical Structure| 85057-78-9

[ 85057-78-9 ]

5-(Ethoxycarbonyl)-3,4-dimethyl-1H-pyrrole-2-carboxylic acid

Similarity: 0.97

Chemical Structure| 2199-46-4

[ 2199-46-4 ]

Ethyl 3,4,5-trimethyl-1H-pyrrole-2-carboxylate

Similarity: 0.97

Chemical Structure| 4391-99-5

[ 4391-99-5 ]

Ethyl 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxylate

Similarity: 0.97

Chemical Structure| 33317-03-2

[ 33317-03-2 ]

Methyl 4,5-dimethyl-1H-pyrrole-2-carboxylate

Similarity: 0.97