14173-30-9|3-Hydroxy-2-pyridinemethanol hydrochloride| Ambeed

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Quality Control of [ 14173-30-9 ] Purity: 95% SDS Specification

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Product Details of [ 14173-30-9 ]

CAS No. :	14173-30-9
Formula :	C₆H₈ClNO₂
M.W :	161.59
SMILES Code :	OCC1=NC=CC=C1O.[H]Cl
MDL No. :	MFCD00006349
InChI Key :	SKVRYQUMKJQZFN-UHFFFAOYSA-N
Pubchem ID :	3084185

Safety of [ 14173-30-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302+H312+H332-H315-H319-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of [ 14173-30-9 ]

* 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 [ 14173-30-9 ]

[ 14173-30-9 ] Synthesis Path-Downstream 1~35

1
[ 25542-62-5 ]
[ 14173-30-9 ]
[ 99156-18-0 ]

References: [1]Farmaco, Edizione Scientifica,1985,vol. 40,p. 630 - 644.
[2]Arzneimittel-Forschung/Drug Research,1986,vol. 36,p. 1561 - 1563.

2
[ 14173-30-9 ]
[ 100-44-7 ]
[ 6059-29-6 ]

References: [1]Tetrahedron,2005,vol. 61,p. 643 - 655.
[2]European Journal of Medicinal Chemistry,1991,vol. 26,p. 455 - 460.

3
[ 40997-78-2 ]
[ 14173-30-9 ]
[ 403729-94-2 ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 902 - 910.

4
[ 14173-30-9 ]
[ 79-44-7 ]
[ 403729-90-8 ]
2-[[(dimethylamino)carbonyl]oxy]methyl-3-hydroxypyridine [ No CAS ]
2-[[(dimethylamino)carbonyl]oxy]methyl-3-[[(dimethylamino)carbonyl]oxy]pyridine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4510 - 4514.
[2]Journal of Medicinal Chemistry,2002,vol. 45,p. 902 - 910.

5
[ 100-39-0 ]
[ 14173-30-9 ]
[ 6059-29-6 ]

Yield	Reaction Conditions	Operation in experiment
58%	With potassium hydroxide; In ethanol;	The starting material was prepared as follows: To a suspension of <strong>[14173-30-9]3-hydroxy-2-hydroxymethylpyridine hydrochloride</strong> (7.0 g, 12.4 mmol) in ethanol (37.5 ml) was added a solution of KOH pellets (85% 1.6 g, 24.7 mmol) in ethanol (25 ml). The reaction was stirred for 5 minutes at ambient temperature and then benzyl bromide was added (2.11 g, 12.36 mmol). The reaction mixture was stirred at ambient temperature for 48 hours, filtered and evaporated. The residue was purified by chromatography (EtOAc, CH2 Cl2) to give 3-benzyloxy-2-hydroxymethylpyridine as a colourless solid (1.55 g, 58%) ›J. Med. Chem., 15, (1972) 615! m.p. 78.7-79.2 C. MS (CI+):216 [M+H]+

References: [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 4431 - 4447.
[2]Patent: US5811459,1998,A .

6
[ 4399-47-7 ]
[ 14173-30-9 ]
[3-(cyclobutyloxy)pyridin-2-yl]methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In water; N,N-dimethyl-formamide;	a 3-Cyclobutyloxy-2-pyridinemethanol 3-Hydroxy-2-(hydroxymethyl)pyridine hydrochloride (1.57 g, 0.009 mol), potassium carbonate (8.09 g, 0.058 mol) and cyclobutyl bromide (5.0 g, 0.037 mol) were stirred together under nitrogen in N,N-dimethylformamide (20 ml) at 50 C. overnight. Water (40 ml) was added, and the resultant solution was acidified to pH 1 with hydrochloric acid (5 N). The solution was washed with dichloromethane (3100 ml), basified to pH 14 with sodium hydroxide solution (4 N), and extracted with dichloromethane (3100 ml). The organic layers from the extraction were combined, washed with water (1*100 ml), dried over magnesium sulfate and concentrated in uacuo to give a dark brown solid which was recrystallized from hexane to give the title compound (0.44 g). 1H NMR (250 MHz, CDCl3) δ 1.61-1.81 (1H, m), 1.86-1.91 (1H, m), 2.09-2.22 (2H, m), 2.39-2.51 (2H, m), 4.31 (1H, br s), 4.66 (1H, m), 4.74 (1H, s), 6.97 (1H, m), 7.07-7.17 (1H, m), 8.13 (1H, m); MS (ES+) m/e 180 [MH]+.

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1367 - 1383.
[2]Patent: US6476030,2002,B1 .

7
[ 14173-30-9 ]
2-hydroxymethyl-piperidin-3-ol; hydrochloride [ No CAS ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 2629 - 2661.

8
[ 14173-30-9 ]
[ 75-03-6 ]
[ 62734-03-6 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1367 - 1383.

9
[ 14173-30-9 ]
[ 18162-48-6 ]
[ 848774-86-7 ]

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 2383 - 2400.
[2]Journal of Medicinal Chemistry,2005,vol. 48,p. 1367 - 1383.

10
[ 14173-30-9 ]
[ 7051-34-5 ]
[ 202931-77-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In water; dimethyl sulfoxide;	a 3-Cyclopropylmethyloxy-2-hydroxymethyl Pyridine Potassium hydroxide (5.2 g, 0.093 mol) was ground to a powder under nitrogen, added to DMSO (30 ml) and stirred for 20 min under nitrogen at room temperature. The mixture was cooled to 0 C. and 3-hydroxy-2-hydroxymethyl pyridine hydrochloride (5.0 g, 0.031 mol) was added. The slurry was stirred at 0 C. for 1 h before the addition of cyclopropylmethyl bromide (3.01 ml, 4.2 g, 0.031 mol). The mixture was allowed to warm to room temperature and stirred under nitrogen overnight. Water (100 ml) was added, and the resultant solution was acidified to pH 1 with hydrochloric acid (5 N). The solution was washed with dichloromethane (3100 ml), basified to pH 14 with sodium hydroxide solution (4 N), and washed again with dichloromethane (3100 ml). The organic layers from the second extraction were combined, washed with water (1100 ml) and saturated sodium chloride solution (1100 ml), dried over magnesium sulfate and concentrated in vacuo to give 3-cyclopropylmethyloxy-2-hydroxymethyl pyridine as a dark brown solid (2.40 g). 1H NMR (250 MHz, CDCl3) δ 0.35 (2H, m), 0.65 (2H, m), 1.26 (1H, m), 3.85 (2H, d, J=6.8 Hz), 4.33 (1H, br s), 4.77 (2H, s), 7.13 (2H, m), 8.13 (2H, m); MS (ES+) m/e 180 [MH]+.

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1367 - 1383.
[2]Patent: US6255305,2001,B1 .

11
[ 14173-30-9 ]
[ 6482-24-2 ]
[3-(2-methoxyethoxy)pyridin-2-yl]methanol [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1367 - 1383.

12
[ 14173-30-9 ]
[ 74-88-4 ]
[ 51984-46-4 ]

Yield	Reaction Conditions	Operation in experiment
7%	With potassium hydroxide; In water; dimethyl sulfoxide;	a 3-Methoxy(2-hydroxymethyl)pyridine To a mixture of ground potassium hydroxide (10.2 g, 0.186 mol) in dimethylsulphoxide (15 ml) under nitrogen was added 3-hydroxy(2-hydroxymethyl)pyridine hydrochloride (5.0 g, 0.031 mol) in dimethylsulphoxide (15 ml) over 0.25 h. The reaction was stirred at room temperature for 1 h before the addition of methyl iodide (1.92 ml, 0.0309 mol) and then stirred at room temperature overnight. Water (100 ml) was added and the solution acidified to pH 1 with 2N hydrochloric acid, washed with dichloromethane (3) and then basified with solid potassium carbonate until pH 12 was attained. The aqueous was extracted with dichloromethane (3), dried (MgSO4), evaporated in vacuo and the residue purified by chromatography on silica gel, eluding with dichloromethane/methanol/ammonia (90:5:0.5), to give the title-compound (300 mg, 7%). 1H NMR (360 MHz, CDCl3) δ 3.85 (3H, s, CH3), 4.74 (2H, s, CH2), 7.12 (1H, d, J=8.3 Hz, Ar-H), 7.21 (1H, m, Ar-H), 8.15 (1H, d, J=4.8 Hz, Ar-H).

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1367 - 1383.
[2]Tetrahedron,2005,vol. 61,p. 643 - 655.
[3]Patent: US6200975,2001,B1 .

13
[ 14173-30-9 ]
[ 1849-55-4 ]

References: [1]Helvetica Chimica Acta,2006,vol. 89,p. 1959 - 1970.
[2]RSC Advances,2016,vol. 6,p. 39627 - 39635.
[3]Chemistry - A European Journal,2010,vol. 16,p. 3510 - 3523.
[4]Inorganic Chemistry,2011,vol. 50,p. 8869 - 8878.

14
[ 14173-30-9 ]
[ 839711-82-9 ]

References: [1]Tetrahedron,2005,vol. 61,p. 643 - 655.

15
[ 14173-30-9 ]
(2R,3S)-ethyl 3-(3-(benzyloxy)-N-oxypyridin-2-yl)-2,3-dihydroxypropanoate [ No CAS ]

References: [1]Tetrahedron,2005,vol. 61,p. 643 - 655.

16
[ 14173-30-9 ]
(2S,3R)-ethyl 3-(3-(benzyloxy)-N-oxypyridin-2-yl)-2,3-dihydroxypropanoate [ No CAS ]

References: [1]Tetrahedron,2005,vol. 61,p. 643 - 655.

17
[ 14173-30-9 ]
[ 1849-53-2 ]

References: [1]Tetrahedron,2005,vol. 61,p. 643 - 655.

18
[ 14173-30-9 ]
[ 94454-57-6 ]

References: [1]Tetrahedron,2005,vol. 61,p. 643 - 655.
[2]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 4431 - 4447.
[3]European Journal of Medicinal Chemistry,1991,vol. 26,p. 455 - 460.

19
[ 14173-30-9 ]
[ 139745-98-5 ]

References: [1]Tetrahedron,2005,vol. 61,p. 643 - 655.

20
[ 14173-30-9 ]
[ 139745-90-7 ]

References: [1]Tetrahedron,2005,vol. 61,p. 643 - 655.

21
[ 14173-30-9 ]
(Z)-isopropyl 3-(3-methoxypyridin-2-yl)acrylate [ No CAS ]

References: [1]Tetrahedron,2005,vol. 61,p. 643 - 655.

22
[ 14173-30-9 ]
[ 102438-91-5 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1367 - 1383.

23
[ 14173-30-9 ]
[ 848774-89-0 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1367 - 1383.

24
[ 14173-30-9 ]
[ 848774-88-9 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1367 - 1383.

25
[ 14173-30-9 ]
[ 848774-87-8 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1367 - 1383.

26
[ 14173-30-9 ]
C₂₄H₂₃N₅O₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1367 - 1383.

27
[ 14173-30-9 ]
C₂₃H₂₁N₅O₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1367 - 1383.

28
[ 14173-30-9 ]
3-phenyl-6-(3-ethoxy-2-pyridyl)methyloxy-7,8,9,10-tetrahydro-(7,10-ethano)-1,2,4-triazolo[3,4-a]phthalazine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1367 - 1383.

29
[ 14173-30-9 ]
C₂₆H₂₇N₅O [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1367 - 1383.

30
[ 14173-30-9 ]
C₂₆H₂₇N₅O₃ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1367 - 1383.

31
[ 14173-30-9 ]
C₂₇H₂₇N₅O₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1367 - 1383.

32
[ 14173-30-9 ]
[ 202929-85-9 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1367 - 1383.

33
[ 14173-30-9 ]
rac-trans-2-(hydroxymethyl)-1-methylpiperidin-3-ol [ No CAS ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 2629 - 2661.

34
[ 14173-30-9 ]
1-benzyl-2-(hydroxymethyl)piperidin-3-ol [ No CAS ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 2629 - 2661.

35
[ 14173-30-9 ]
rac-cis-1-benzyl-2-(hydroxymethyl)piperidin-3-ol [ No CAS ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 2629 - 2661.

Historical Records

Technical Information

• Appel Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Hydride Reductions • Jones Oxidation • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Preparation of Alcohols • Preparation of Amines • Reactions of Alcohols • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Swern Oxidation

Similar Product of
[ 14173-30-9 ]

A605842 [14047-53-1]

2-(Hydroxymethyl)pyridin-3-ol

Reason: Free-salt

Related Functional Groups of
[ 14173-30-9 ]

Alcohols

A206210 [14187-25-8]

(3-Hydroxypyridine-2,6-diyl)dimethanol hydrochloride

Similarity: 0.98

A605842 [14047-53-1]

2-(Hydroxymethyl)pyridin-3-ol

Similarity: 0.98

A176096 [42097-42-7]

2-(Hydroxymethyl)-6-methylpyridin-3-ol

Similarity: 0.96

A830203 [38029-16-2]

(3-Hydroxypyridine-2,6-diyl)dimethanol

Similarity: 0.96

A614033 [188670-04-4]

2-(Methoxymethyl)pyridin-3-ol

Similarity: 0.94

Related Parent Nucleus of
[ 14173-30-9 ]

Pyridines

A206210 [14187-25-8]

(3-Hydroxypyridine-2,6-diyl)dimethanol hydrochloride

Similarity: 0.98

A605842 [14047-53-1]

2-(Hydroxymethyl)pyridin-3-ol

Similarity: 0.98

A176096 [42097-42-7]

2-(Hydroxymethyl)-6-methylpyridin-3-ol

Similarity: 0.96

A830203 [38029-16-2]

(3-Hydroxypyridine-2,6-diyl)dimethanol

Similarity: 0.96

A614033 [188670-04-4]

2-(Methoxymethyl)pyridin-3-ol

Similarity: 0.94

Precautionary Statements-General
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H200	Unstable explosive
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H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 14173-30-9

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