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[ CAS No. 584-08-7 ] {[proInfo.proName]}

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Chemical Structure| 584-08-7
Chemical Structure| 584-08-7
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Product Details of [ 584-08-7 ]

CAS No. :584-08-7 MDL No. :MFCD00011382
Formula : CK2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :BWHMMNNQKKPAPP-UHFFFAOYSA-L
M.W : 138.21 Pubchem ID :11430
Synonyms :
Chemical Name :Potassium carbonate

Calculated chemistry of [ 584-08-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 6.77
TPSA : 63.19 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -0.13
Log Po/w (WLOGP) : -2.45
Log Po/w (MLOGP) : -1.6
Log Po/w (SILICOS-IT) : -0.44
Consensus Log Po/w : -0.92

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.61
Solubility : 33.5 mg/ml ; 0.243 mol/l
Class : Very soluble
Log S (Ali) : -0.74
Solubility : 25.0 mg/ml ; 0.181 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 1.49
Solubility : 4260.0 mg/ml ; 30.8 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.25

Safety of [ 584-08-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P501 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 584-08-7 ]

* 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.

  • Upstream synthesis route of [ 584-08-7 ]
  • Downstream synthetic route of [ 584-08-7 ]

[ 584-08-7 ] Synthesis Path-Upstream   1~60

  • 1
  • [ 100-48-1 ]
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  • [ 41050-96-8 ]
Reference: [1] Patent: US4406897, 1983, A,
  • 2
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  • [ 71962-74-8 ]
  • [ 498-95-3 ]
YieldReaction ConditionsOperation in experiment
55% With Ki In ethyl acetate; acetone The [(2-chloroethoxy)-methylene]bis[4-chlorobenzene] as prepared in PREPARATION II above (11.02 g), ethyl 3-piperidinecarboxylate (5.49 g), KI (0.3 g), and K2 CO3 (9.73 g) are placed in 120 ml acetone and refluxed for about 63 hr. TLC (silica, 30percent ethyl acetate:
70percent hexane as eluent) is used to monitor completion of reaction.
The contents are cooled, and acetone is removed.
The residual oil is dissolved in ether, and washed with H2 O, brine, then dried over MgSO4.
The ether is evaporated to an oil (16 g) which is chromatographed on silica using 25percent ethyl acetate: 75percent hexane as eluent.
8.13 g of the desired product, 3-piperidinecarboxylic acid, 1-[2-[bis(4-chlorophenyl)methoxy]ethyl]-, ethyl ester, is obtained for a 55percent yield. NMR spectrum is consistent with that expected for product.
Reference: [1] Patent: US4910312, 1990, A,
  • 3
  • [ 120-43-4 ]
  • [ 584-08-7 ]
  • [ 75-26-3 ]
  • [ 4318-42-7 ]
Reference: [1] Patent: US5354747, 1994, A,
[2] Patent: US5461047, 1995, A,
  • 4
  • [ 4704-77-2 ]
  • [ 584-08-7 ]
  • [ 36236-76-7 ]
YieldReaction ConditionsOperation in experiment
53.5% With sulfuric acid In acetone EXAMPLE 21
(+-)-N-(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl-N,N-dimethyl-β-hydroxyethyl ammonium bromide
Into a 500 milliliter round bottom flask equipped with a magnetic stir bar and drying tube, a solution of 28.0 grams (0.181 mole) of 3-bromo-1,2-propanediol in 200 milliliters of acetone was added.
Then, 0.5 milliliter of concentrated sulfuric acid was added and the reaction allowed to proceed at room temperature for 24 hours with continuous stirring.
The reaction mixture was neutralized with 13.0 grams of K2 CO3 for 30 minutes, the solution was filtered and the solvent evaporated in vacuo.
The resulting oil was dissolved in 150 milliliter of ether, extracted three times with 150 milliliter portions of water and the organic layer dried over anhydrous sodium sulfate.
The filtered ether was evaporated in vacuo and 100 milliliters of hexanes was added, resulting in two layers.
The upper layer was decanted and evaporated in vacuo to provide 19.1 grams (53.5percent) of (2,2-dimethyl-1,3-dioxolan-4-yl)methyl bromide.
Reference: [1] Patent: US5614548, 1997, A,
  • 5
  • [ 616-45-5 ]
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  • [ 77-78-1 ]
  • [ 5264-35-7 ]
Reference: [1] Patent: WO2005/7157, 2005, A1, . Location in patent: Page/Page column 39
  • 6
  • [ 75-09-2 ]
  • [ 584-08-7 ]
  • [ 5625-67-2 ]
YieldReaction ConditionsOperation in experiment
75% With trifluoroacetic acid In ethanol Step 3:
1-(2-Phenylpropyl)piperazin-2-one
In the same way as that described in Example 2, Step 3, using 2-[(bromoacetyl)(2-phenylpropyl)amino]ethyl carbamic acid tert-butyl ester (1.64 g, 4.11 mmol), trifluoroacetic acid (4 mL) and CH2 Cl2 (40 mL), followed by K2 CO3 (1.1 g, 8.2 mmol) and EtOH (100 mL).
The piperazinone (668 mg, 75percent) was isolated as a colourless oil. 1 H NMR (250 MHz, CDCl3) δ1.28 (3H, d, J=6.8 Hz), 2.72-2.93 (3H, m), 3.04-3.26 (3H, m), 3.28 (1H, d, J=17.3 Hz), 3.52 (1H, d, J=17.3 Hz), 3.85-3.93 (1H, m), 7.19-7.35 (5H, m).
Reference: [1] Patent: US5998415, 1999, A,
  • 7
  • [ 5470-18-8 ]
  • [ 13061-96-6 ]
  • [ 584-08-7 ]
  • [ 18699-87-1 ]
Reference: [1] Patent: US5869676, 1999, A,
  • 8
  • [ 584-08-7 ]
  • [ 105-56-6 ]
  • [ 873-83-6 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 12, p. 1167 - 1172
  • 9
  • [ 5332-24-1 ]
  • [ 124-38-9 ]
  • [ 584-08-7 ]
  • [ 6480-68-8 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 43, p. 13426 - 13430[2] Angew. Chem., 2017, vol. 129, p. 13611 - 13615,5
  • 10
  • [ 5006-66-6 ]
  • [ 7789-69-7 ]
  • [ 584-08-7 ]
  • [ 74-95-3 ]
  • [ 26218-78-0 ]
Reference: [1] Patent: US5420270, 1995, A,
  • 11
  • [ 63837-11-6 ]
  • [ 124-38-9 ]
  • [ 584-08-7 ]
  • [ 24851-69-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 43, p. 13426 - 13430[2] Angew. Chem., 2017, vol. 129, p. 13611 - 13615,5
  • 12
  • [ 110-89-4 ]
  • [ 584-08-7 ]
  • [ 107-91-5 ]
  • [ 109-94-4 ]
  • [ 4241-27-4 ]
Reference: [1] Patent: US5521179, 1996, A,
  • 13
  • [ 584-08-7 ]
  • [ 609-15-4 ]
  • [ 20485-39-6 ]
YieldReaction ConditionsOperation in experiment
31% With formamide In benzene EXAMPLE 1
Preparation of Ethyl 4-Methyl-5-Oxazolecarboxylate
This compound was prepared according to the procedure described in French Pat. No. 1,543,853.
A mixture of 50.0 g (0.337 moles) of ethyl chloroacetoacetate and 42.0 g (0.933 moles) of formamide was stirred at 120°-135° for 18 hr.
Thereafter, the mixture was cooled using an ice bath to 10° C. 300 ml of 1 N K2 CO3 was added dropwise with gas evolution noted.
After complete addition of K2 CO3 solution, the reaction mixture was stirred with 200 ml of benzene/ether (2:1) and saturated with NaCl.
The insoluble material was filtered and the benzene/ether layer was separated and washed with water, dried (MgSO4) and concentrated under reduced pressure.
The brown residue was distilled on a Kugelrohr to give 14.8 g of white solid, mp 31°-33° C.; yield 31percent; nmr (CDCl3) 8.0 (s,1H,C2 H), 44 (q, J=7 Hz, 2H,CH2), 2.5 (s,3H,CH3), 1.4 (t,3H,CH3).
Reference: [1] Patent: US4303439, 1981, A,
  • 14
  • [ 288-32-4 ]
  • [ 1194-02-1 ]
  • [ 584-08-7 ]
  • [ 25372-03-6 ]
Reference: [1] Patent: US5736548, 1998, A,
  • 15
  • [ 75-09-2 ]
  • [ 584-08-7 ]
  • [ 2258-42-6 ]
  • [ 5270-94-0 ]
Reference: [1] Patent: US5276152, 1994, A,
  • 16
  • [ 591-20-8 ]
  • [ 584-08-7 ]
  • [ 100-44-7 ]
  • [ 53087-13-1 ]
Reference: [1] Patent: US5952350, 1999, A,
[2] Patent: US5843940, 1998, A,
  • 17
  • [ 118-45-6 ]
  • [ 584-08-7 ]
  • [ 1823-59-2 ]
Reference: [1] Patent: WO2009/120212, 2009, A1, . Location in patent: Page/Page column 34-39
  • 18
  • [ 584-08-7 ]
  • [ 151477-57-5 ]
  • [ 100704-10-7 ]
Reference: [1] Patent: US5440047, 1995, A,
  • 19
  • [ 110-53-2 ]
  • [ 584-08-7 ]
  • [ 2050-94-4 ]
Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10774 - 10777
  • 20
  • [ 1634-04-4 ]
  • [ 6638-79-5 ]
  • [ 584-08-7 ]
  • [ 79-04-9 ]
  • [ 67442-07-3 ]
Reference: [1] Patent: US5786515, 1998, A,
  • 21
  • [ 99-66-1 ]
  • [ 584-08-7 ]
  • [ 2695-47-8 ]
  • [ 13319-71-6 ]
Reference: [1] Patent: US4238389, 1980, A,
  • 22
  • [ 124-38-9 ]
  • [ 51437-00-4 ]
  • [ 584-08-7 ]
  • [ 403-15-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 43, p. 13426 - 13430[2] Angew. Chem., 2017, vol. 129, p. 13611 - 13615,5
  • 23
  • [ 2420-16-8 ]
  • [ 584-08-7 ]
  • [ 74-88-4 ]
  • [ 4903-09-7 ]
Reference: [1] Patent: US6031003, 2000, A,
[2] Patent: US5763569, 1998, A,
[3] Patent: US5688938, 1997, A,
  • 24
  • [ 586-30-1 ]
  • [ 584-08-7 ]
  • [ 3556-83-0 ]
Reference: [1] Patent: US4532343, 1985, A,
  • 25
  • [ 586-30-1 ]
  • [ 584-08-7 ]
  • [ 121-44-8 ]
  • [ 3556-83-0 ]
Reference: [1] Patent: US6127356, 2000, A,
  • 26
  • [ 37687-57-3 ]
  • [ 584-08-7 ]
  • [ 5417-17-4 ]
YieldReaction ConditionsOperation in experiment
96% With sodium hydroxide In chloroform; water; acetonitrile Step 2
Synthesis of 2-chloro-3,4-dimethoxybenzaldehyde
184 g (0.986 mol) of 2-chloro-3-hydroxy-4-methoxybenzaldehyde was dissolved in 2 l of CH3 CN. 204 g (1.476 mol) of K2 CO3 and 298 g (2.096 mol) of CH3 I were added to the solution, which was heated under reflux for 4 hours.
After cooling, the crystals were separated by filtration and the mother liquor was concentrated under reduced pressure.
800 ml of water and 600 ml of CHCl3 were added to the residue to conduct extraction.
The CHCl3 layer was washed with 500 ml of 10percent NaOH and a saturated Nacl aqueous solution.
It was dehydrated over MgSO4 and concentrated to dryness under reduced pressure to obtain 189.49 g (96percent) of 2-chloro-3,4-dimethoxybenzaldehyde.
mp 70°~72° C.
NMR (90 MHz, CDCl3) δ:3.88 (3H, s), 3.96 (3H, s), 6.92 (1H, d), 7.72 (1H, d), 10.28 (1H, s)
Reference: [1] Patent: US5292521, 1994, A,
  • 27
  • [ 121-71-1 ]
  • [ 7732-18-5 ]
  • [ 584-08-7 ]
  • [ 100-44-7 ]
  • [ 34068-01-4 ]
Reference: [1] Patent: US4404222, 1983, A,
[2] Patent: US4407819, 1983, A,
  • 28
  • [ 100-39-0 ]
  • [ 584-08-7 ]
  • [ 490-78-8 ]
  • [ 30992-63-3 ]
Reference: [1] Patent: US5248685, 1993, A,
  • 29
  • [ 582-17-2 ]
  • [ 584-08-7 ]
  • [ 3469-26-9 ]
Reference: [1] Patent: US5712312, 1998, A,
  • 30
  • [ 584-08-7 ]
  • [ 106-93-4 ]
  • [ 105-53-3 ]
  • [ 1559-02-0 ]
Reference: [1] Patent: US2010/239576, 2010, A1,
  • 31
  • [ 372-20-3 ]
  • [ 584-08-7 ]
  • [ 75-03-6 ]
  • [ 458-03-7 ]
Reference: [1] Patent: US5593993, 1997, A,
  • 32
  • [ 100-02-7 ]
  • [ 70384-51-9 ]
  • [ 584-08-7 ]
  • [ 6482-24-2 ]
  • [ 22483-40-5 ]
Reference: [1] Patent: US5585394, 1996, A,
  • 33
  • [ 2150-44-9 ]
  • [ 584-08-7 ]
  • [ 74-88-4 ]
  • [ 19520-74-2 ]
Reference: [1] Patent: US5998470, 1999, A,
  • 34
  • [ 50-86-2 ]
  • [ 584-08-7 ]
  • [ 77-78-1 ]
  • [ 4093-29-2 ]
Reference: [1] Patent: US4138492, 1979, A,
  • 35
  • [ 876-02-8 ]
  • [ 584-08-7 ]
  • [ 74-88-4 ]
  • [ 10024-90-5 ]
Reference: [1] Patent: US6001884, 1999, A,
[2] Patent: US6031003, 2000, A,
[3] Patent: US5688938, 1997, A,
[4] Patent: US5763569, 1998, A,
  • 36
  • [ 480-66-0 ]
  • [ 584-08-7 ]
  • [ 100-44-7 ]
  • [ 18065-05-9 ]
Reference: [1] Patent: US4267165, 1981, A,
[2] Patent: US4290957, 1981, A,
[3] Patent: US4348333, 1982, A,
[4] Patent: US4226804, 1980, A,
  • 37
  • [ 1878-67-7 ]
  • [ 584-08-7 ]
  • [ 14062-30-7 ]
Reference: [1] Patent: US6025388, 2000, A,
  • 38
  • [ 584-08-7 ]
  • [ 614-75-5 ]
  • [ 74-88-4 ]
  • [ 27798-60-3 ]
Reference: [1] Patent: US5656629, 1997, A,
  • 39
  • [ 14199-15-6 ]
  • [ 584-08-7 ]
  • [ 100-44-7 ]
  • [ 68641-16-7 ]
Reference: [1] Patent: US4672071, 1987, A,
[2] Patent: US4761420, 1988, A,
  • 40
  • [ 3943-89-3 ]
  • [ 100-39-0 ]
  • [ 584-08-7 ]
  • [ 1570-05-4 ]
YieldReaction ConditionsOperation in experiment
92% With potassium hydroxide In methanol; water; butanone (B)
3,4-DIBENZYLOXYBENZOIC ACID
To 60 g (0.33 mole) of ethyl 3,4-dihydroxybenzoate in 50 ml of methyl ethyl ketone was added 105.5 g (0.76 mole) of K2 CO3 and 168.8 g (0.76 mole) of benzyl bromide.
The mixture was refluxed for 16 hours and filtered.
Evaporation of the filtration gave an oil.
This oil was mixed with 40 g of KOH, 350 ml of water and 350 ml of methanol and refluxed for 2.5 hours.
The methanol was evaporated and the reaction mixture was acidified with concentrated HCl.
The precipitate was filtered to give 101 g (92percent) of the desired product; m.p. 184°-185° C.
The NMR and IR spectra were consistent with the assigned structure.
92% With potassium hydroxide In methanol; water; butanone 3,4-Dibenzyloxybenzoic Acid
To 60 g (0.33 mole) of ethyl 3,4-dihydroxybenzoate in 50 ml of methyl ethyl ketone was added 105.5 g (0.76 mole) of K2 CO3 and 168.8 g (0.76 mole) of benzyl bromide.
The mixture was refluxed for 16 hours and filtered.
Evaporation of the filtration gave an oil.
This oil was mixed with 40 g of KOH, 350 ml of water and 350 ml of methanol and refluxed for 2.5 hours.
The methanol was evaporated and the reaction mixture was acidified with concentrated HCl.
The precipitate was filtered to give 101 g (92percent) of the desired product; m.p. 184°-5° C.
The NMR and IR spectra were consistent with the assigned structure.
92% With potassium hydroxide In methanol; water; butanone (b)
3,4-Dibenzyloxybenzoic Acid
To 60 g (0.33 mole) of ethyl 3,4-dihydroxybenzoate in 50 ml of methyl ethyl ketone was added 105.5 g (0.76 mole) of K2 CO3 and 168.8 g (0.76 mole) of benzyl bromide.
The mixture was refluxed for 16 hours and filtered.
Evaporation of the filtration gave an oil.
This oil was mixed with 40 g of KOH, 350 ml of water and 350 ml of methanol and refluxed for 2.5 hours.
The methanol was evaporated and the reaction mixture was acidified with concentrated HCl.
The precipitate was filtered to give 101 g (92percent) of the desired product; m.p. 184°-185° C.
The NMR and IR spectra were consistent with the assigned structure.
Reference: [1] Patent: US4582855, 1986, A,
[2] Patent: US4402974, 1983, A,
[3] Patent: US4798892, 1989, A,
  • 41
  • [ 3964-56-5 ]
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  • [ 50638-47-6 ]
Reference: [1] Patent: US5739166, 1998, A,
  • 42
  • [ 124-38-9 ]
  • [ 584-08-7 ]
  • [ 5391-88-8 ]
  • [ 97364-15-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 43, p. 13426 - 13430[2] Angew. Chem., 2017, vol. 129, p. 13611 - 13615,5
  • 43
  • [ 3262-72-4 ]
  • [ 584-08-7 ]
  • [ 2766-43-0 ]
Reference: [1] Patent: US5380945, 1995, A,
  • 44
  • [ 1722-12-9 ]
  • [ 57260-73-8 ]
  • [ 584-08-7 ]
  • [ 137583-05-2 ]
Reference: [1] Patent: US6159964, 2000, A,
  • 45
  • [ 584-08-7 ]
  • [ 72537-17-8 ]
  • [ 89402-42-6 ]
Reference: [1] Patent: US4625035, 1986, A,
[2] Patent: US4480102, 1984, A,
  • 46
  • [ 124-38-9 ]
  • [ 584-08-7 ]
  • [ 72537-17-8 ]
  • [ 89402-42-6 ]
Reference: [1] Patent: US4480102, 1984, A,
  • 47
  • [ 584-08-7 ]
  • [ 147-85-3 ]
  • [ 27957-91-1 ]
Reference: [1] Patent: US5424444, 1995, A,
[2] Patent: US5508418, 1996, A,
[3] Patent: US5516912, 1996, A,
  • 48
  • [ 124-38-9 ]
  • [ 584-08-7 ]
  • [ 25216-74-4 ]
  • [ 111331-82-9 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 43, p. 13426 - 13430[2] Angew. Chem., 2017, vol. 129, p. 13611 - 13615,5
  • 49
  • [ 181955-94-2 ]
  • [ 584-08-7 ]
  • [ 7757-82-6 ]
  • [ 85817-34-1 ]
YieldReaction ConditionsOperation in experiment
78% With sodium cyanoborohydride; benzaldehyde; acetic acid In tetrahydrofuran; methanol 3.
4-Benzyl-2-hydroxymethylpiperazine
To a cooled (0° C.) and stirred solution of Intermediate 1 (22 g, 57 mmol), acetic acid (9.7 mL, 171 mmol) and sodium cyanoborohydride (7.16 g, 114 mmol) in methanol (440 mL) was added benzaldehyde (5.8 mL, 57 mmol).
The cooling bath was removed and the mixture stirred at room temperature for 3 h.
Saturated K2 CO3 solution (200 mL) was added and the mixture stirred for 15 min.
The solvents were evaporated and the residue partitioned between CH2 Cl2 (2*400 mL) and water (500 mL).
The combined organic layers were dried (Na2 SO4) and evaporated.
The residue was chromatographed on silica gel, eluding with CH2 Cl2: MeOH (95:5) to afford an inseparable mixture of 4-benzylpiperazine-2-carboxylic acid methyl ester and the corresponding ethyl ester (5.33 g, 40percent), in a 7:1 ratio respectively.
To a solution of the esters (5.33 g, 22.8 mmol) in THF (200 mL) was added LiAl H4 (22.8 mL of a 1.0M solution in ether) dropwise at -10° C.
Stirring was continued at -10° C. for 2.5 h.
After this time saturated Na2 SO4 solution (30 mL) was added and the cooling bath removed.
Stirring was continued at room temperature for 10 min then the mixture was filtered and the filtrate evaporated.
The residue was chromatographed on silica gel, eluding with CH2 Cl2:MeOH:NH3 (90:8:1-->60:8:1) to afford the title compound (3.7 g, 78percent) as a colourless oil. 1 H NMR (360 MHz, CDCl3) δ 1.89-1.95 (1H, m), 2.08-2.30 (3H, m), 2.68-2.71 (2H, m), 2.86-3.04 (3H, m), 3.45-3.60 (4H, m), 7.13-7.32 (5H, m). MS (ES+) 207 (M+1).
Reference: [1] Patent: US5849746, 1998, A,
  • 50
  • [ 110-85-0 ]
  • [ 610-94-6 ]
  • [ 584-08-7 ]
  • [ 159974-63-7 ]
Reference: [1] Patent: US6159990, 2000, A,
  • 51
  • [ 584-08-7 ]
  • [ 216309-28-3 ]
  • [ 153286-94-3 ]
Reference: [1] Patent: US2008/70931, 2008, A1, . Location in patent: Page/Page column 12
  • 52
  • [ 7732-18-5 ]
  • [ 584-08-7 ]
  • [ 501-53-1 ]
  • [ 2584-71-6 ]
  • [ 155075-23-3 ]
Reference: [1] Patent: US5436229, 1995, A,
  • 53
  • [ 7732-18-5 ]
  • [ 584-08-7 ]
  • [ 501-53-1 ]
  • [ 2584-71-6 ]
  • [ 155075-23-3 ]
Reference: [1] Patent: US5578574, 1996, A,
  • 54
  • [ 57-55-6 ]
  • [ 584-08-7 ]
  • [ 16606-55-6 ]
Reference: [1] Patent: US6054596, 2000, A,
  • 55
  • [ 100704-10-7 ]
  • [ 497-19-8 ]
  • [ 584-08-7 ]
  • [ 101066-61-9 ]
YieldReaction ConditionsOperation in experiment
67% With N-Bromosuccinimide In ethyl acetate b
2-Chloro4-pyridinecarboxaldehyde
A suspension of 2-chloro-4-hydroxymethylpyridine (8.0 g, 55.9 mmol), NBS (14.9 g, 83.9 mmol), and K2 CO3 (11.75 g, 97.1 mmol) in ethyl acetate was refluxed for 3 h.
Another portion of NBS (14.9 g, 83.9 mmol) and Na2 CO3 (12.0 g, 114 mmol) was added and heating was continued another 3.5 h.
The reaction mixture was cooled, filtered through a pad of celite, concentrated under reduced and chromatographed with 0.5-4percent CH3 OH/CH2 Cl2.
The combined fractions were washed with NaHCO3 (sat.), 10percent Na2 S2 O3, and NaCl (sat.), dried, filtered and evaporated to give the title compound as a light yellow solid (5.3 g, 67percent yield).
1 H NMR (CDCl3): δ10.06 (s, 1H), 8.66 (d, 1H, J=5.0 Hz), 7.76 (s, 1H), 7.66 (d, 1H, J=5.0 Hz).
67% With N-Bromosuccinimide In ethyl acetate b
2-Chloro-4-pyridinecarboxaldehyde
A suspension of 2-chloro-4-hydroxymethylpyridine (8.0 g, 55.9 mmol), NBS (14.9 g, 83.9 mmol), and K2 CO3 (11.75 g, 97.1 mmol) in ethyl acetate was refluxed for 3 h.
Another portion of NBS (14.9 g, 83.9 mmol) and Na2 CO3 (12.0 g, 114 mmol) was added and heating was continued another 3.5 h.
The reaction mixture was cooled, filtered through a pad of celite, concentrated under reduced and chromatographed with 0.5-4percent CH3 OH/CH2 Cl2.
The combined fractions were washed with NaHCO3 (sat.), 10percent Na2 S2 O3, and NaCl (sat.), dried, filtered and evaporated to give the title compound as a light yellow solid (5.3 g, 67percent yield).
1 H NMR (CDCl3): δ10.06 (s, 1H), 8.66 (d, 1H, J=5.0 Hz), 7.76 (s, 1H), 7.66 (d, 1H,J=5.0 Hz).
Reference: [1] Patent: US5977103, 1999, A,
[2] Patent: US5756499, 1998, A,
  • 56
  • [ 100704-10-7 ]
  • [ 497-19-8 ]
  • [ 584-08-7 ]
  • [ 101066-61-9 ]
YieldReaction ConditionsOperation in experiment
67% With N-Bromosuccinimide In ethyl acetate b
2-Chloro-4-pyridinecarboxaldehyde
A suspension of 2-chloro-4-pyridinemethanol (8.0 g, 55.9 mmol), NBS (14.9 g, 83.9 mmol), and K2 CO3 (11.75 g, 97.1 mmol) in EtOAc was refluxed for 3 h.
A Second portion of NBS (14.9 g, 83.9 mmol) and Na2 CO3 (12.0 g, 114 mmol) were added and the reaction was heated to reflux for an additional 3.5 h, cooled and filtered through a pad of celite.
The filtrate, after concentrattion to a small volume, was subjected to flash chromatography eluding with 0.5-4percent CH3 OH/CH2 Cl2.
The fractions containing product were combined, washed successively with sat aq NaHCO3 10percent Na2 S2 O3, and brine, dried (MgSO4) and concentrated in vacuo to give the title compound as a light yellow solid; yield 5.3 g (67percent).
1 H NMR (CDCl3) δ 10.06 (s, 1H), 8.66 (d, 1H, J=5.0 Hz), 7.76 (s, 1H), 7.66 (d, 1H, J=5.0 Hz).
67% With N-Bromosuccinimide In ethyl acetate b
2-Chloro-4-pyridinecarboxaldehyde
A suspension of 2-chloro-4-pyridinemethanol (8.0 g, 55.9 mmol), NBS (14.9 g, 83.9 mmol), and K2 CO3 (11.75 g, 97.1 mmol) in EtOAc was refluxed for 3 h.
A second portion of NBS (14.9 g, 83.9 mmol) and Na2 CO3 (12.0 g, 114 mmol) were added and the reaction was heated to reflux for an additional 3.5 h, cooled and filtered through a pad of celite.
The filtrate, after concentration to a small volume, was subjected to flash chromatography eluding with 0.5-4percent CH3 OH/CH2 Cl2.
The fractions containing product were combined, washed successively with sat aq NaHCO3 10percent Na2 S2 O3, and brine, dried (MgSO4) and concentrated in vacuo to give the title compound as a light yellow solid; yield 5.3 g (67percent).
1 H NMR,,(CDCl3) δ 10.06 (s, 1H), 8.66 (d, 1H, J=5.0 Hz), 7.76 (s, 1H), 7.66 (d, 1H, J=5.0 Hz).
Reference: [1] Patent: US5658903, 1997, A,
[2] Patent: US5739143, 1998, A,
  • 57
  • [ 53250-83-2 ]
  • [ 504-02-9 ]
  • [ 584-08-7 ]
  • [ 75-86-5 ]
  • [ 99105-77-8 ]
Reference: [1] Patent: US5318947, 1994, A,
  • 58
  • [ 110-91-8 ]
  • [ 119312-61-7 ]
  • [ 584-08-7 ]
  • [ 119313-12-1 ]
Reference: [1] Patent: US5077402, 1991, A,
  • 59
  • [ 2457-50-3 ]
  • [ 7677-24-9 ]
  • [ 584-08-7 ]
  • [ 79-44-7 ]
  • [ 159307-02-5 ]
Reference: [1] Patent: US5350696, 1994, A,
[2] Patent: US5559214, 1996, A,
[3] Patent: US5760191, 1998, A,
  • 60
  • [ 124-38-9 ]
  • [ 41604-19-7 ]
  • [ 584-08-7 ]
  • [ 137045-30-8 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 43, p. 13426 - 13430[2] Angew. Chem., 2017, vol. 129, p. 13611 - 13615,5
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