[ CAS No. 21427-61-2 ] {[proInfo.proName]}

Name: 21427-61-2|5-Chloro-2-hydroxy-3-nitropyridine|95%
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SKU: A208914
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Quality Control of [ 21427-61-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 21427-61-2 ]

Product Details of [ 21427-61-2 ]

CAS No. :	21427-61-2	MDL No. :	MFCD00114884
Formula :	C₅H₃ClN₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QVGQNICXNZMXQA-UHFFFAOYSA-N
M.W :	174.54	Pubchem ID :	248048
Synonyms :

Calculated chemistry of [ 21427-61-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	40.09
TPSA :	78.94 Å²

Pharmacokinetics

GI absorption :	High
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) :	-6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.92
Log Po/w (XLOGP3) :	1.84
Log Po/w (WLOGP) :	1.35
Log Po/w (MLOGP) :	0.52
Log Po/w (SILICOS-IT) :	-0.53
Consensus Log Po/w :	0.82

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.42
Solubility :	0.665 mg/ml ; 0.00381 mol/l
Class :	Soluble
Log S (Ali) :	-3.12
Solubility :	0.133 mg/ml ; 0.000762 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.44
Solubility :	6.29 mg/ml ; 0.0361 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.91

Safety of [ 21427-61-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 21427-61-2 ]

* 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.

Upstream synthesis route of [ 21427-61-2 ]
Downstream synthetic route of [ 21427-61-2 ]

[ 21427-61-2 ] Synthesis Path-Upstream 1~13

1
[ 21427-61-2 ]
[ 98027-36-2 ]

Reference： [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 3, p. 1222 - 1237
[2] Chemical and Pharmaceutical Bulletin, 1958, vol. 6, p. 46,48
[3] Patent: WO2006/51410, 2006, A1, . Location in patent: Page/Page column 42-43
[4] Patent: EP2471792, 2012, A1, . Location in patent: Page/Page column 45

2
[ 21427-61-2 ]
[ 78607-32-6 ]

Reference： [1] Journal of the Chemical Society, 1952, p. 2042,2044
[2] Journal of the Chemical Society, 1952, p. 2042,2044

3
[ 21427-61-2 ]
[ 90902-83-3 ]

Reference： [1] Journal of the Chemical Society, 1952, p. 2042,2044

4
[ 21427-61-2 ]
[ 21427-62-3 ]

Reference： [1] Journal of the Chemical Society, 1952, p. 2042,2044
[2] Roczniki Chemii, 1968, vol. 42, p. 2079,2084[3] Chem.Abstr., 1969, vol. 70, p. 106327
[4] Yakugaku Zasshi, 1952, vol. 72, p. 431[5] Chem.Abstr., 1953, p. 6404
[6] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1980, vol. 16, # 12, p. 1234 - 1238[7] Khimiya Geterotsiklicheskikh Soedinenii, 1980, vol. 16, # 12, p. 1632 - 1636
[8] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 1, p. 73 - 76
[9] Patent: WO2005/97805, 2005, A1, . Location in patent: Page/Page column 57-58
[10] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 13, p. 3983 - 3987

5
[ 75-44-5 ]
[ 21427-61-2 ]
[ 21427-62-3 ]

Reference： [1] Patent: US5274100, 1993, A,

6
[ 21427-61-2 ]
[ 21427-62-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 10, p. 2625 - 2637

7
[ 5409-39-2 ]
[ 21427-61-2 ]
[ 21427-62-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 10, p. 2625 - 2637

8
[ 21427-61-2 ]
[ 75806-86-9 ]

Reference： [1] Journal of the Chemical Society, 1952, p. 2042,2044

9
[ 21427-61-2 ]
[ 181123-11-5 ]

Reference： [1] Journal of the Chemical Society, 1952, p. 2042,2044

10
[ 1072-98-6 ]
[ 21427-61-2 ]

Yield	Reaction Conditions	Operation in experiment
80.5%	With sulfuric acid; nitric acid; sodium nitrite In ice-water; water	EXAMPLE A2 Preparation of 5-chloro-2-hydroxy-3-nitropyridine STR9 321 g of 5-chloro-2-aminopyridine are added dropwise to 1.25 l of concentrated sulfuric acid. The reaction mixture is then stirred until the educt has completely dissolved. Then 172.5 g of sodium nitrite, dissolved in 240 ml of water, are added at a temperature of 40°-45° C. and the reaction mixture is stirred for 15 minutes. Subsequently 125 ml of 100percent nitric acid are added dropwise at 50° C. over 40 minutes. The reaction mixture is kept for 1 hour at 55° C. and then poured onto 5 kg of ice-water. The product in the form of a yellow precipitate is isolated by filtration, washed copiously with water and subsequently dried at 60° C., giving 351 g of 5-chloro-2-hydroxy-3-nitropyridine (80.5percent of theory) with a melting point of 229°-231° C.

Reference： [1] Patent: US5274100, 1993, A,
[2] Yakugaku Zasshi, 1952, vol. 72, p. 431[3] Chem.Abstr., 1953, p. 6404

11
[ 4214-79-3 ]
[ 21427-61-2 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 13, p. 3983 - 3987

12
[ 5409-39-2 ]
[ 21427-61-2 ]

Reference： [1] Journal of the American Pharmaceutical Association (1912-1977), 1949, vol. 38, p. 70
[2] Journal of the Chemical Society, 1951, p. 2590,2593

13
[ 1072-98-6 ]
[ 7664-93-9 ]
[ 7697-37-2 ]
[ 21427-61-2 ]

Reference： [1] Yakugaku Zasshi, 1952, vol. 72, p. 431[2] Chem.Abstr., 1953, p. 6404

[ 21427-61-2 ] Synthesis Path-Downstream 1~82

1
[ 1072-98-6 ]
[ 21427-61-2 ]

Yield	Reaction Conditions	Operation in experiment
80.5%	With sulfuric acid; nitric acid; sodium nitrite; In ice-water; water;	EXAMPLE A2 Preparation of 5-chloro-2-hydroxy-3-nitropyridine STR9 321 g of 5-chloro-2-aminopyridine are added dropwise to 1.25 l of concentrated sulfuric acid. The reaction mixture is then stirred until the educt has completely dissolved. Then 172.5 g of sodium nitrite, dissolved in 240 ml of water, are added at a temperature of 40-45 C. and the reaction mixture is stirred for 15 minutes. Subsequently 125 ml of 100% nitric acid are added dropwise at 50 C. over 40 minutes. The reaction mixture is kept for 1 hour at 55 C. and then poured onto 5 kg of ice-water. The product in the form of a yellow precipitate is isolated by filtration, washed copiously with water and subsequently dried at 60 C., giving 351 g of 5-chloro-2-hydroxy-3-nitropyridine (80.5% of theory) with a melting point of 229-231 C.

Reference： [1]Patent: US5274100,1993,A
[2]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1952,vol. 72,p. 431
Chem.Abstr.,1953,p. 6404

2
[ 5409-39-2 ]
[ 21427-61-2 ]

Reference： [1]Journal of the American Pharmaceutical Association (1912),1949,vol. 38,p. 70

3
[ 21427-61-2 ]
[ 98027-36-2 ]

Yield	Reaction Conditions	Operation in experiment
	With water; iron; calcium chloride; In ethanol; for 2.0h;Heating / reflux;	Intermediate 4; 3-amino-5-chloropyridin-2-ol; To a 500 mL round bottom flask charged with 5-chloro-2-hydroxy-3-nitro pyridine (4.9 g, 28.7 mmol), Fe (7.2 g, 129.7 mmol) and CaCI2 (2.86 g, 25.8 mmol) was added 4:1 EtOHiH2O (50 mL) and the mixture was heated at reflux for 2h. After cooling to room temperature the mixture was filtered through a celite pad and washed with ethanol/water. EPO <DP n="44"/>The dark filtrate was evaporated and dried in vacuum for 2h to afford 3-amino-5-chloropyridin- 2-ol. LCMS: m/e 145 (M+1).
	With water; iron; calcium chloride; In ethanol; at 20℃; for 1.5h;Reflux;	(Reference Example 8-1) To an 80% aqueous ethanol suspension (150 ml) of 5-chloro-3-nitropyridin-2-ol (15.0 g) and calcium chloride (9.54 g) was added iron powder (24.0 g), followed by stirring at room temperature for 30 minutes, and further under heating at reflux for 1 hour. After the temperature was brought back to room temperature, the reaction suspension was filtered through Celite. Water was added to the filtrate, and extracted 8 times with a methanol-dichloromethane (1:10) mixed solvent. The collected organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 3-amino-5-chloropyridin-2-ol (8.86 g). 1H NMR (400 MHz, DMSO-D6) delta: 5.43 (s, 2H), 6.38 (d, 1H, J = 2.7 Hz), 6.72 (d, 1H, J = 2.7 Hz), 11.52 (s, 1H).
20 g	With iron; ammonium chloride; In ethanol; water; at 90℃; for 2.0h;	a) 3-amino-5-chloropyridin-2-ol A mixture of 5-chloro-3-nitropyridin-2-ol (30.0 g), iron (14.5 g), ammonium chloride (46.5 g) and ethanol/water (300 mL, 3/1, v/v) was stirred at 90 C. for 2 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (20.0 g). MS: [M+H]+ 145.3.

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 1222 - 1237
[2]Chemical and pharmaceutical bulletin,1958,vol. 6,p. 46,48
[3]Patent: WO2006/51410,2006,A1 .Location in patent: Page/Page column 42-43
[4]Patent: EP2471792,2012,A1 .Location in patent: Page/Page column 45
[5]Patent: US2019/169166,2019,A1 .Location in patent: Paragraph 1118; 1119

4
[ 21427-61-2 ]
[ 21427-62-3 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; In DMF (N,N-dimethyl-formamide); at 110℃; for 0.5h;	Example 10; (+/-)-9-[Acetyl-(3,5-bis-trifluoromethylbenzyl)amino]-3-chloro-2-methoxy-6,7,8,9- tetrahydro-pyrido[3,2-b]azepine-5-carboxylic acid isopropyl ester; Step 1;. Preparation of 5-Chloro-3-nitro-pyridine-2-carbonitrile; Add 3-nitro-5-chloro-pyridin-2-ol (3.9 g, 22.3 mmol) to a mixture of phosphorous oxychloride (4.17 mL) and dimethylformamide (10 mL). Heat the resulting mixture at 110 C for 30 min. Cool the reaction mixture to room temperature and pour onto ice- water. Add sodium bicarbonate slowly until neutralization occurs and extract with ethyl acetate. Dry the organic layer over anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure. Dissolve the residue in N-methyl pyrrolidinone (4 mL), add copper (I) cyanide (2.39 g, 26.7 mmol) and heat at 160 C for 15 min. Cool the reaction mixture to room temperature and pour onto ice water and ethyl acet ate. Add a saturated solution of sodium bicarbonate, separate the organic layer, and extract the aqueous layer with ethyl acetate. Dry the combined organic layers over sodium sulfate, filter, and concentrate under reduced pressure. Purify the residue using silica gel chromatography, eluting with ethyl acetate/hexanes 1: 3 to afford the title cornpound (1.01 g, 26%). H-NMR (CDC13, 300 MHz) : No. 8.61 (s, 1H), 8.95 (s, 1H).

Reference： [1]Journal of the Chemical Society,1952,p. 2042,2044
[2]Roczniki Chemii,1968,vol. 42,p. 2079,2084
    Chem.Abstr.,1969,vol. 70,p. 106327
[3]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1952,vol. 72,p. 431
    Chem.Abstr.,1953,p. 6404
[4]Chemistry of Heterocyclic Compounds,1980,vol. 16,p. 1234 - 1238
    Khimiya Geterotsiklicheskikh Soedinenii,1980,vol. 16,p. 1632 - 1636
[5]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 73 - 76
[6]Patent: WO2005/97805,2005,A1 .Location in patent: Page/Page column 57-58
[7]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3983 - 3987

5
[ 21427-61-2 ]
[ 75806-86-9 ]

Reference： [1]Journal of the Chemical Society,1952,p. 2042,2044

6
[ 21427-61-2 ]
5-chloro-1-methyl-3-nitro-1H-pyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To 5-choro-2-hydroxy-3-nitropyridine (15.0 g, 86 mmo) in DMF (200 m) at 0C was added NaH (4.13 g, 103 mmo) in portions and the reaction mixture was stirred at 0C for lh. odomethane (806 rn, 129 mmo) was added and the mixture was stirred at RT for 4h. The mixture was concentrated, water was added and the mixture was extracted with AcOEt, The organic phase was washed with brine, dried over Na2SO4 and evaporated to dryness to afford 5-choro-1-methy-3-nitropyridin-2(IH)-one. Mz = 189-191 [M+H]+, Rt = 0.55 mm (U PLC Method B4).

Reference： [1]Journal of the Chemical Society,1951,p. 2590,2593
[2]Patent: WO2015/181747,2015,A1 .Location in patent: Page/Page column 79; 80

9
[ 1072-98-6 ]
[ 7664-93-9 ]
[ 7697-37-2 ]
[ 21427-61-2 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1952,vol. 72,p. 431
Chem.Abstr.,1953,p. 6404

10
[ 21427-61-2 ]
[ 21427-62-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2625 - 2637

11
[ 5409-39-2 ]
[ 21427-61-2 ]
[ 21427-62-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2625 - 2637

12
[ 21427-61-2 ]
[ 136122-52-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 73 - 76

13
[ 21427-61-2 ]
[ 136122-48-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 73 - 76

14
[ 21427-61-2 ]
β,β-dimethyl-6-chloro-3-((4-chlorophenyl)methyl)-3H-imidazo(4,5-b)pyridine-2-butanoic acid [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 73 - 76

15
[ 21427-61-2 ]
[ 77064-54-1 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1980,vol. 16,p. 1234 - 1238
Khimiya Geterotsiklicheskikh Soedinenii,1980,vol. 16,p. 1632 - 1636

16
[ 21427-61-2 ]
[ 3493-98-9 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1980,vol. 16,p. 1234 - 1238
Khimiya Geterotsiklicheskikh Soedinenii,1980,vol. 16,p. 1632 - 1636

17
[ 21427-61-2 ]
[ 78607-32-6 ]

Reference： [1]Journal of the Chemical Society,1952,p. 2042,2044
[2]Journal of the Chemical Society,1952,p. 2042,2044

18
[ 21427-61-2 ]
[ 90902-83-3 ]

Reference： [1]Journal of the Chemical Society,1952,p. 2042,2044

19
[ 21427-61-2 ]
[ 408538-29-4 ]

Reference： [1]Journal of the Chemical Society,1952,p. 2042,2044

20
[ 21427-61-2 ]
[ 27330-34-3 ]

Reference： [1]Journal of the Chemical Society,1952,p. 2042,2044

21
[ 21427-61-2 ]
[ 181123-11-5 ]

Reference： [1]Journal of the Chemical Society,1952,p. 2042,2044

22
[ 21427-61-2 ]
[ 856834-36-1 ]

Reference： [1]Journal of the Chemical Society,1952,p. 2042,2044

23
[ 21427-61-2 ]
[ 107-18-6 ]
[ 865716-68-3 ]

Yield	Reaction Conditions	Operation in experiment
15%	With PS-triphenylphosphane; di-tert-butyl-diazodicarboxylate; In tetrahydrofuran; at 20℃;	Example 99A 2-(allyloxy)-5-chloro-3-nitropyridine To a mixture of <strong>[21427-61-2]5-chloro-3-nitro-pyridin-2-ol</strong> (0.600 g, 3.4 mmol), DBAD (1.19 g, 5.16 mmol), triphenylphosphine-polymer supported (3 mmol/g, 1.70 g, 5.16 mmol) in THF (18 mL) was added allyl alcohol (0.42 mL, 6.12 mmol). The reaction mixture was stirred at room temperature overnight, filtered through celite, and concentrated. The residue was purified by flash chromatography eluding with hexane/ethyl acetate (95:5 to 1:1) to give 0.120 g (15%) of the desired product. MS (DCI/NH3) m/z: 214.9 (M+H)+; 1H NMR (300 MHz, CDCl3) delta ppm 5.01 (ddd, J=5.34, 1.40, 1.40 Hz, 2H) 5.32 (dd, J=10.51, 1.36 Hz, 1H) 5.49 (dd, J=17.12, 1.53 Hz, 1H) 6.06 (m, 1H) 8.28 (d, J=2.37 Hz, 1H) 8.34 (d, J=2.37 Hz, 1H).

Reference： [1]Patent: US2005/215556,2005,A1 .Location in patent: Page/Page column 85

24
[ 75-44-5 ]
[ 21427-61-2 ]
[ 21427-62-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	In hexane; N,N-dimethyl-formamide; toluene;	EXAMPLE A3 Preparation of 2,5-dichloro-3-nitropyridine STR10 75 g of phosgene are introduced at a temperature of 85-95 C. over 1 hour into a mixture of 87.5 g of 5-chloro-2-hydroxy-3-nitropyridine in 500 ml of toluene and 3 ml of N,N-dimethylformamide. The reaction mixture is kept for 2 hours under reflux at 85-95 C. and then allowed to cool to room temperature over a period of 18 hours. The reaction mixture is washed 3 times with water and the organic phase is dried over sodium sulfate and thereafter concentrated by evaporation. The crude product, obtained in the form of a brown oil, is crystallized from 200 ml of n-hexane, giving 67.5 g of 2,5-dichloro-3-nitropyridine (70% of theory) with a melting point of 38-39 C.

Reference： [1]Patent: US5274100,1993,A

25
[ 1250768-37-6 ]
[ 21427-61-2 ]
C₁₃H₁₁ClN₄O₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 537 - 542

26
[ 21427-61-2 ]
[ 1268841-93-5 ]

Reference： [1]Patent: EP2471792,2012,A1

27
[ 21427-61-2 ]
[ 1268841-91-3 ]

Reference： [1]Patent: EP2471792,2012,A1

28
[ 4214-79-3 ]
[ 21427-61-2 ]