[ CAS No. 337957-59-2 ]

Name: 337957-59-2|1-(p-Tolyl)-1H-pyrazole-4-carbaldehyde|98%
Brand: Ambeed
SKU: A835763
Price: 40.0 USD
Availability: InStock
Rating: 99 (26 reviews)

{[proInfo.proName]} ,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 337957-59-2

Structure of 337957-59-2 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Bulk Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 100K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 337957-59-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 337957-59-2 ]

SDS Specification

Alternatived Products of [ 337957-59-2 ]

Product Details of [ 337957-59-2 ]

CAS No. :	337957-59-2	MDL No. :	MFCD03426978
Formula :	C₁₁H₁₀N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LFWZUGUMUQRWIU-UHFFFAOYSA-N
M.W :	186.21	Pubchem ID :	820137
Synonyms :

Calculated chemistry of [ 337957-59-2 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.09
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	53.92
TPSA :	34.89 Å²

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) :	-6.21 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.9
Log Po/w (XLOGP3) :	1.72
Log Po/w (WLOGP) :	1.99
Log Po/w (MLOGP) :	1.36
Log Po/w (SILICOS-IT) :	2.12
Consensus Log Po/w :	1.82

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.53
Solubility :	0.553 mg/ml ; 0.00297 mol/l
Class :	Soluble
Log S (Ali) :	-2.07
Solubility :	1.59 mg/ml ; 0.00854 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.26
Solubility :	0.101 mg/ml ; 0.000545 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.53

Safety of [ 337957-59-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 337957-59-2 ]

* 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 [ 337957-59-2 ]

[ 337957-59-2 ] Synthesis Path-Downstream 1~30

1
[ 33513-42-7 ]
N-Eth-(Z)-ylidene-N'-p-tolyl-hydrazine [ No CAS ]
[ 337957-59-2 ]

Yield	Reaction Conditions	Operation in experiment
42%	With trichlorophosphate at 90℃; for 3h;

Reference： [1]Chornous; Bratenko; Vovk [Chemistry of Heterocyclic Compounds, 2006, vol. 42, # 9, p. 1242 - 1243]

2
[ 100-97-0 ]
[ 539-44-6 ]
[ 337957-59-2 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid

Reference： [1]Location in patent: scheme or table De Oliveira, Aline Lima; Alves De Oliveira, Carlos Henrique; Mairink, Laura Maia; Pazini, Francine; Menegatti, Ricardo; Liao, Luciano Morais [Magnetic Resonance in Chemistry, 2011, vol. 49, # 8, p. 537 - 542]

3
[ 337957-59-2 ]
[ 95-54-5 ]
[ 1373836-35-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	In ethanol for 4h; Reflux;

Reference： [1]Location in patent: experimental part Ren, Tie-Gang; Cheng, Hong-Bin; Zhang, Jing-Lai; Li, Wei-Jie; Jia, Guo; Yang, Li-Rong [Journal of Fluorescence, 2012, vol. 22, # 1, p. 201 - 212]

4
[ 20518-17-6 ]
[ 100-97-0 ]
[ 337957-59-2 ]

Yield	Reaction Conditions	Operation in experiment
97.6%	With trifluoroacetic acid for 12h; Reflux; chemoselective reaction;

Reference： [1]De Oliveira; Mairink; Pazini; Liao; De Oliveira; Viegas Jr.; De Oliveira; Cunha; Oliveira; Paz Jr.; Eberlin; Menegatti, Ricardo [Synthetic Communications, 2013, vol. 43, # 12, p. 1633 - 1639]

5
[ 826-81-3 ]
[ 337957-59-2 ]
[ 108-24-7 ]
[ 1612877-16-3 ]

Yield	Reaction Conditions	Operation in experiment
	at 160℃; for 96h; Autoclave;	General procedure for preparing (E)-2-(2-(1-aryl-1H-pyrazol-4-yl)vinyl)quinolin-8-ol General procedure: 5 mmol 1-Arylpyrazole-4-carbaldehyde, 5 mmol 2-methyl-8-hydroxyl quinoline and 20 mL acetic anhydride were stirred and sealed in a Teflon-lined stainless steel autoclave (25 mL), kept at 160 °C for 4 days and then cooled to room temperature. Resultant mixed solution was poured into 100 mL H2O, followed by extractionwith CH2Cl2 (3 50 mL) and rotary evaporation to remove solvent. As-separated crystalline precipitates were dissolved in 25 mL DMF, followed by dropwise addition of 20 mL of aqueous HCl (volume fraction: 36%) at 80 °C in a reaction period of 5 h. Then the reactants were allowed to react for additional 4 h after 25 mL of triethylamine was added dropwise. Upon completion of the reaction, the hot mixture was poured into ice water (250 mL) and stirred overnight, followed by extraction with CH2Cl2 (4 100 mL).The combined organic layers were washed with saturated NaCl solution and dried with anhydrous Na2SO4. Crude mixed products were obtained after residual solvent was evaporated under reduced pressure, and as-obtained crude products were purified by column chromatography (silica gel, ethyl acetate/petroleum ether).

Reference： [1]Ren, Tiegang; Wang, Jie; Li, Guihui; Cheng, Hongbin; Li, Yongzhe [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2014, vol. 129, p. 7 - 13]

6
[ 337957-59-2 ]
[ 1612877-07-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 96 h / 160 °C / Autoclave 2: hydrogenchloride / N,N-dimethyl-formamide; water / 5 h / 80 °C 3: triethylamine / 4 h

Reference： [1]Ren, Tiegang; Wang, Jie; Li, Guihui; Cheng, Hongbin; Li, Yongzhe [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2014, vol. 129, p. 7 - 13]

7
[ 20518-17-6 ]
[ 33513-42-7 ]
[ 337957-59-2 ]

Yield	Reaction Conditions	Operation in experiment
66.9 g	Stage #1: N,N-dimethyl-formamide With trichlorophosphate at -5 - 0℃; for 0.5h; Stage #2: 1-(4-methylphenyl)-1H-pyrazole at 90℃; for 15h;	2.2 2) 1- (4-methylphenyl) lH-pyrazole-4-carbaldehyde Take 185ml (2.4mol) N, N- dimethylformamide in three 1000ml flask, mechanical stirring at ice bath temperature the reaction system was maintained at -5 -0 . 10min After dropping 225ml (2.4mol) of phosphorus oxychloride. After the addition was complete the reaction was continued 30min. After addition of 94.8g (0.6mol) 1- (4- methylphenyl) lH-pyrazole, the reaction temperature was raised to 90 deg.] C for 15 hours. After completion of the reaction was monitored by TLC, the reaction solution was poured into ice water, stirred, made basic with aqueous sodium carbonate, aqueous phase extracted with (3 × 150ml) and extracted with ethyl acetate, the combined organic phase was dried over anhydrous magnesium sulfate, filtered off solution. The residue was purified by column chromatography (eluent, ethyl acetate and petroleum ether, the volume ratio of 1: 5) was isolated as a white solid 66.9g.
16.5 g	With trichlorophosphate at 0 - 110℃; for 10.5h; Inert atmosphere;	1.2 1-(p-tolyl)-1H-pyrazole-4-carbaldehyde POCI3 (87.29 g, 569.33 mmol, 5.0 equiv.) was slowly added to DMF (41.61 g, 569.33 mmol, 5.0 equiv.) at 0 to 10°C under nitrogen atmosphere. This was then stirred for 15 minutes. To this mixture, a solution of 1- (p-tolyl ) -IJJ-pyrazole (18.0 g, 113.86 mmol, 1.0 equiv.) in DMF (25 ml) was slowly added and the reaction mixture was then stirred at 0 to 10°C for 30 minutes. Then the resulting mixture was brought to room temperature and heated to 110°C for 10 h . After cooling to room temperature , the reaction mixture was slowly poured into distilled water and pH of the reaction mixture was made basic by adding 10% NaOH solution to it. The product was then extracted with ethyl acetate (3 x 100 mL) . The combined organic layer was washed with distilled water , dried over sodium sulfate, filtered and concentrated under reduced pressure to give a crude product. The crude product thus obtained was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to afford 1- (p-tolyl ) -lff-pyrazole-4-carbaldehyde as a light yellow solid (16.5 g, Yield 78%) . (0449) 1H NMR (CDC13) : 9.96 (s, 1H) , 8.39 (s, 1H) , 8.15 (s, 1H) , 7.59 (d, J= 8.4 Hz, 2H) , 7.30-7.29 (m, 2H) , 2.41 (s, 3H) ; MS (M+l) 187.13.

Reference： [1]Current Patent Assignee: JIANGSU YANGNONG CHEMICAL CO., LTD. - CN105777717, 2016, A Location in patent: Paragraph 0367; 0368; 0369
[2]Current Patent Assignee: OAT AGRIO CO., LTD.; OAT & IIL INDIA LABORATORIES PRIVATE LIMITED - WO2020/3219, 2020, A1 Location in patent: Page/Page column 50-51

8
[ 337957-59-2 ]
[ 851180-85-3 ]

Yield	Reaction Conditions	Operation in experiment
86.1%	With sodium tetrahydroborate; ethanol at 20℃; Cooling with ice;	2.3 3) Preparation of (1- (4-methylphenyl) lH-pyrazol-4-yl) methanol The 18.6g (0.1mol) 1- (4- methylphenyl) lH-pyrazole-4-carbaldehyde was dissolved in 150ml of absolute ethanol, under ice-cooling with stirring. To the reaction flask was added 5 minutes after portionwise 9.5g (0.25mol) of sodium borohydride, followed by reaction at room temperature for 4-6 hours. After completion of the reaction was monitored by TLC, most of the ethanol was distilled off under reduced pressure, stirring the reaction was poured into water, the aqueous phase with (3 × 50ml) and extracted with ethyl acetate, the combined organic phase was dried over anhydrous magnesium sulfate, filtered, exsolution. The residue was purified by column chromatography (eluent, ethyl acetate and petroleum ether, the volume ratio of 1: 2) to separate 16.2 g of a white solid, a yield of 86.1%.
75%	With 3-chloro-benzenecarboperoxoic acid In chloroform for 4h; Inert atmosphere; Reflux;	1.3 1-(p-tolyl)-1H-pyrazole-4-ol m-Chloroperbenzoic acid (8.34 g, 48.36 mmol, 0.9 equiv.) was added to a solution of 1- (p-tolyl ) -lff-pyrazole-4-carbaldehyde (10.0 g, 53.74 mmol, 1.0 equiv.) in chloroform (500 mL) at room temperature under nitrogen atmosphere. The resulting mixture was refluxed for 4h. The reaction mixture was then cooled to room temperature, diluted with DCM (100 mL) , washed with sodium bicarbonate solution (3 x 100 mL) followed by distilled water (3 x 100 mL) , dried over sodium sulfate, filtered and concentrated under reduced pressure to give a crude product . Methanol (50 mL), distilled water (25 mL) , followed by concentrated HC1 (50 mL) was added to the crude product and then the reaction mixture was refluxed for lOh. After cooling to room temperature, all volatiles were distilled-off under reduced pressure . The pH of the reaction mixture was then made neutral by adding sodium bicarbonate solution and extracted with ethyl acetate (3 x 100 mL) . The combined organic layer was washed with distilled water , dried over sodium sulfate, filtered and concentrated under reduced pressure to give a crude product. The crude product thus obtained was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to afford 1- (p-tolyl ) -lJJ-pyrazol-4-ol as a light brown solid (7.0 g, Yield 75%) . (0452) NMR (CDC13) : 7.56 (s, 1H) , 7.46 (d, J= 8.4 Hz, 2H) , 7.41 (s, 1H) , 7.22 (d, J = 8.4 Hz, 2H) , 4.86 (bs, 1H) , 2.36 (s, 3H) ; MS (M+l) 175.13.

Reference： [1]Current Patent Assignee: JIANGSU YANGNONG CHEMICAL CO., LTD. - CN105777717, 2016, A Location in patent: Paragraph 0370; 0371; 0372
[2]Current Patent Assignee: OAT AGRIO CO., LTD.; OAT & IIL INDIA LABORATORIES PRIVATE LIMITED - WO2020/3219, 2020, A1 Location in patent: Page/Page column 51-52

9
[ 337957-59-2 ]
4-(chloromethyl)-1-(4-methylphenyl)-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: ethanol; sodium tetrahydroborate / 20 °C / Cooling with ice 2: thionyl chloride / toluene / Reflux

Reference： [1]Current Patent Assignee: JIANGSU YANGNONG CHEMICAL CO., LTD. - CN105777717, 2016, A

10
[ 337957-59-2 ]
C₁₆H₁₅ClN₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: ethanol; sodium tetrahydroborate / 20 °C / Cooling with ice 2: thionyl chloride / toluene / Reflux 3: potassium carbonate / N,N-dimethyl-formamide / 100 °C

Reference： [1]Current Patent Assignee: JIANGSU YANGNONG CHEMICAL CO., LTD. - CN105777717, 2016, A

11
[ 337957-59-2 ]
1-(2-chlorobenzyl)-4-(((1-(p-tolyl)-1H-pyrazol-4-yl)oxy)methyl)-1H-1,2,3-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 2 h / 60 - 70 °C 2.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / 0 °C 2.2: 0.5 h / 0 - 20 °C 3.1: copper(ll) sulfate pentahydrate; sodium L-ascorbate / <i>tert</i>-butyl alcohol; water / 2 h / 20 °C

Reference： [1]Madhavilatha; Fatima, Narjis; Sabitha, Gowravaram; Reddy, B. V. Subba; Yadav; Bhattacharjee, Debanjan; Jain, Nishant [Medicinal Chemistry Research, 2017, vol. 26, # 8, p. 1753 - 1763]

12
[ 337957-59-2 ]
1-(2-bromobenzyl)-4-(((1-(p-tolyl)-1H-pyrazol-4-yl)oxy)methyl)-1H-1,2,3-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 2 h / 60 - 70 °C 2.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / 0 °C 2.2: 0.5 h / 0 - 20 °C 3.1: copper(ll) sulfate pentahydrate; sodium L-ascorbate / <i>tert</i>-butyl alcohol; water / 2 h / 20 °C

13
[ 337957-59-2 ]
1-(4-methoxybenzyl)-4-(((1-(p-tolyl)-1H-pyrazol-4-yl)oxy)methyl)-1H-1,2,3-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 2 h / 60 - 70 °C 2.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / 0 °C 2.2: 0.5 h / 0 - 20 °C 3.1: copper(ll) sulfate pentahydrate; sodium L-ascorbate / <i>tert</i>-butyl alcohol; water / 2 h / 20 °C

14
[ 337957-59-2 ]
3-(4-methoxybenzyl)-5-(((1-(p-tolyl)-1H-pyrazol-4-yl)oxy)methyl)isoxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 2 h / 60 - 70 °C 2.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / 0 °C 2.2: 0.5 h / 0 - 20 °C 3.1: triethylamine; sodium hypochlorite / dichloromethane / 0.5 h / 0 °C 3.2: 0 - 20 °C

15
[ 337957-59-2 ]
[ 77458-34-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With 3-chloro-benzenecarboperoxoic acid In chloroform at 60 - 70℃; for 2h;	Step 1 General procedure: To a solution of 1,3-diphenylpyrazole-4-carboxaldehyde(1b, 10 g, 0.04mol) in chloroform (100mL) wasadded mCPBA (13.91 g, 0.08 mol) and the reaction mixturewas heated to 60-70 °C for 2 h. After completion of thereaction as followed by TLC, the reaction mixture was cooledto room temperature (RT) and washed with 10% Na2CO3solution (2×50mL) (to remove excess mCPBA). Theorganic layer was separated, dried over anhydrous sodiumsulphate and concentrated in vacuo to give 9.5 g of residue.

16
[ 337957-59-2 ]
4-(prop-2-yn-1-yloxy)-1-(p-tolyl)-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 2 h / 60 - 70 °C 2.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / 0 °C 2.2: 0.5 h / 0 - 20 °C

17
[ 337957-59-2 ]
[ 1234174-16-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / Inert atmosphere; Reflux 2: caesium carbonate / N,N-dimethyl-formamide / 10 h / 70 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: OAT AGRIO CO., LTD.; OAT & IIL INDIA LABORATORIES PRIVATE LIMITED - WO2020/3219, 2020, A1

18
[ 337957-59-2 ]
[ 1234174-17-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / Inert atmosphere; Reflux 2: caesium carbonate / N,N-dimethyl-formamide / 10 h / 70 °C / Inert atmosphere 3: ammonium chloride; zinc / tetrahydrofuran; methanol; water / 2 h / 20 °C

Reference： [1]Current Patent Assignee: OAT AGRIO CO., LTD.; OAT & IIL INDIA LABORATORIES PRIVATE LIMITED - WO2020/3219, 2020, A1

19
[ 337957-59-2 ]
2,3-dimethyl-6-((1-(p-tolyl)-1H-pyrazol-4-yl)oxy)quinolin-4(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / Inert atmosphere; Reflux 2: caesium carbonate / N,N-dimethyl-formamide / 10 h / 70 °C / Inert atmosphere 3: ammonium chloride; zinc / tetrahydrofuran; methanol; water / 2 h / 20 °C 4: toluene-4-sulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 16 h / Inert atmosphere; Dean-Stark; Reflux

Reference： [1]Current Patent Assignee: OAT AGRIO CO., LTD.; OAT & IIL INDIA LABORATORIES PRIVATE LIMITED - WO2020/3219, 2020, A1

20
[ 337957-59-2 ]
2,3-dimethyl-6-((1-(p-tolyl)-1H-pyrazol-4-yl)oxy)quinolin-4-yl methyl carbonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / Inert atmosphere; Reflux 2.1: caesium carbonate / N,N-dimethyl-formamide / 10 h / 70 °C / Inert atmosphere 3.1: ammonium chloride; zinc / tetrahydrofuran; methanol; water / 2 h / 20 °C 4.1: toluene-4-sulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 16 h / Inert atmosphere; Dean-Stark; Reflux 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere 5.2: 10 h / 20 °C

Reference： [1]Current Patent Assignee: OAT AGRIO CO., LTD.; OAT & IIL INDIA LABORATORIES PRIVATE LIMITED - WO2020/3219, 2020, A1

21
[ 337957-59-2 ]
2,3-dimethyl-6-((1-(p-tolyl)-1H-pyrazol-4-yl)oxy)quinolin-4-yl ethyl carbonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / Inert atmosphere; Reflux 2.1: caesium carbonate / N,N-dimethyl-formamide / 10 h / 70 °C / Inert atmosphere 3.1: ammonium chloride; zinc / tetrahydrofuran; methanol; water / 2 h / 20 °C 4.1: toluene-4-sulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 16 h / Inert atmosphere; Dean-Stark; Reflux 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere 5.2: 10 h / 20 °C

Reference： [1]Current Patent Assignee: OAT AGRIO CO., LTD.; OAT & IIL INDIA LABORATORIES PRIVATE LIMITED - WO2020/3219, 2020, A1

22
[ 337957-59-2 ]
C₃₁H₂₈N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydroxide / ethanol / 12 h / 20 °C 2: hydrogenchloride / 8 h / 85 °C