76509-17-6|3-Benzyloxypyridine| Ambeed

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Quality Control of [ 76509-17-6 ] Purity: 98% SDS Specification

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Product Details of [ 76509-17-6 ]

CAS No. :	76509-17-6
Formula :	C₁₂H₁₁NO
M.W :	185.22
SMILES Code :	C1(OCC2=CC=CC=C2)=CC=CN=C1
MDL No. :	MFCD13151998
InChI Key :	LLWFWIZOFFLRKC-UHFFFAOYSA-N
Pubchem ID :	10012635

Safety of [ 76509-17-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 76509-17-6 ]

* 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 [ 76509-17-6 ]

[ 76509-17-6 ] Synthesis Path-Downstream 1~35

1
[ 626-60-8 ]
[ 20194-18-7 ]
[ 76509-17-6 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1419 - 1420.
[2]Journal of Organic Chemistry,1997,vol. 62,p. 503 - 509.

2
[ 3389-21-7 ]
[ 76509-17-6 ]
[ 76509-18-7 ]

References: [1]Tetrahedron,1987,vol. 43,p. 2135 - 2146.
[2]Tetrahedron Letters,1980,vol. 21,p. 2341 - 2344.

3
[ 109-00-2 ]
[ 100-44-7 ]
[ 76509-17-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In dichloromethane;	EXAMPLE 1 Production of 3-benzyloxypyridine (2) To a suspension of 3-hydroxypyridine (24.7 g, 260 mmole) in distilled methylene chloride (260 ml) were added Adogen 464 (1.6 ml), 40% NaOH (130 ml), benzyl chloride (32 ml, 278 mmole), followed by stirring for 3 days at room temperature. The organic layer was separated from the reaction solution, and the aqueous layer was admixed with water and extracted with methylene chloride. The resulting extract was combined with the methylene chloride layer separated previously, and the combined solution was washed with saturated saline, dried over K2 CO3 and freed of the solvent by distillation. The residue was purified on a column of silica gel (7734, n-hexane:ethyl acetate=20:1 to 5:1). Yield of 8.6 g or 17.9%.
	With sodium hydroxide;Adogen 464; In dichloromethane; water; at 20℃;	Step 15.1 : 3-Benzyloxy-pyridine; 9.5 g (10 mMol) 3-Hydroxy-pyridine and 9.45 ml (10 mMol) benzylchloride are dissolved in 50 ml CH2CI2 at rt. 0.5 g Adogen 464 (Aldrich 63393-96-4) are added followed by dropwise addition of 50 ml of aq. NaOH solution (40 %wt). The resulting yellow solution is stirred overnight, leading to formation of a white precipitate. The insolubles are filtered off and the filtrated is diluted with CH2CI2 and H2O. The phases are separated and the aq. phase is repeatedly extracted with CH2CI2. Combined organic extracts are dried, concentrated and the residual crude product is purified by flash chromatography (SiO2, CH2CI2/Me0H 95:5) to give the title compound as a yellow oil: MS: [M+1]+ = 186; 1H MNR (CDCI3): δ ppm 8.42 (s, 1 H), 8.26 (s, 1 H), 7.55-7.38 (m, 5H), 7.30-7.19 (m, 2H), 5.17 (s, 2H).

References: [1]Tetrahedron Letters,1995,vol. 36,p. 2235 - 2238.
[2]Journal of Organic Chemistry,1997,vol. 62,p. 503 - 509.
[3]European Journal of Medicinal Chemistry,2010,vol. 45,p. 2683 - 2688.
[4]Heterocycles,1996,vol. 43,p. 2249 - 2256.
[5]Patent: US5202334,1993,A .
[6]Patent: WO2008/9487,2008,A1 .Location in patent: Page/Page column 68.

4
[ 76509-17-6 ]
[ 105-36-2 ]
3-(benzyloxy)-1-(2-ethoxy-2-oxoethyl)pyridin-1-ium bromide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3636 - 3658.

5
[ 76509-17-6 ]
[ 36016-40-7 ]
2,4,6-trimethyl-benzenesulfonate-1-amino-3-benzyloxy-pyridinium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; dichloromethane; ethyl acetate;	EXAMPLE 2 Production of N-amino-3-benzyloxypyridinium mesitylenesulfonate (3) A solution of O-mesitylenesulfonylhydroxylamine (13.7 g, 44.6 mmole, purity of 70%) in methylene chloride (150 ml) was added dropwise to a solution of <strong>[76509-17-6]3-benzyloxypyridine</strong> (8.25 g, 44.6 mmole) in methylene chloride (150 ml) under ice-cooling, with stirring. The reaction solution was returned to room temperature, stirred for 1 hours and concentrated to one-quarter of the original volume at 20 to 30 C., and ether was added to the concentrate, thereby white crystals were precipitated. This product was used in the next reaction, without being purified. Yield of 14.9 g or 83.3%. The product was recrystallized from a mixed solution of methanol and ethyl acetate to give white flaky crystals having a melting point of 105 to 108 C. Elemental analysis, for C21 H24 O4 N2 S: Calcd.: C, 62.99; H, 6.04; N, 7.00. Found: C, 62.85; H, 6.03; N, 6.71.
	In dichloromethane; at 20℃; for 2h;	Step 15.4: 2,4,6-Trimethyl-benzenesulfonate-1 -amino-3-benzyloxy-pyridinium; 8.75 g (40.6 mMol) O-Mesitylenesulfonylacetohydroxylamine and 4.2 g (22.7 mMol) 3- benzyloxy-pyridine are dissolved in 70 ml CH2CI2 and stirred for 2 h at rt. The reaction mixture is diluted with ether leading to precipitation of the product which is isolated by filtration, washed with ether and dried to give the title compound as a white powder: 1H MNR <n="70"/>(CDCI3): δ ppm 9.01 (s, 1 H), 8.76 (d, 1 H), 7.58 (dd, 1 H), 7.41 (d, 1 H), 7.40-7.38 (m, 5 H), 6.84 (s, 2H), 5.18 (s, 2H), 2.74 (s, 6H), 2.22 (s, 3H).

References: [1]Heterocycles,1996,vol. 43,p. 2249 - 2256.
[2]Patent: US5202334,1993,A .
[3]Patent: WO2008/9487,2008,A1 .Location in patent: Page/Page column 68-69.

6
[ 17747-43-2 ]
[ 100-39-0 ]
[ 76509-17-6 ]

References: [1]Chemistry of Heterocyclic Compounds,1998,vol. 34,p. 40 - 43.

7
[ 372-47-4 ]
[ 100-51-6 ]
[ 76509-17-6 ]

References: [1]Tetrahedron,2002,vol. 58,p. 4931 - 4935.

8
[ 626-60-8 ]
[ 100-51-6 ]
[ 76509-17-6 ]

References: [1]Tetrahedron,2002,vol. 58,p. 4931 - 4935.

9
[ 626-55-1 ]
[ 100-51-6 ]
[ 76509-17-6 ]

References: [1]Journal of Organic Chemistry,2008,vol. 73,p. 9326 - 9333.
[2]Tetrahedron,2002,vol. 58,p. 4931 - 4935.

10
[ 76509-17-6 ]
(1R,3R,4S,8S)-5-Methylene-3-p-tolyl-7-aza-tricyclo[5.3.0.0^4,8]decane [ No CAS ]