6812-16-4|2-Hydroxy-3-methoxybenzonitrile| Ambeed

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Quality Control of [ 6812-16-4 ] Purity: 98% SDS Specification

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Product Details of [ 6812-16-4 ]

CAS No. :	6812-16-4
Formula :	C₈H₇NO₂
M.W :	149.15
SMILES Code :	N#CC1=CC=CC(OC)=C1O
MDL No. :	MFCD02261936
InChI Key :	NILKMGHUFOHVMU-UHFFFAOYSA-N
Pubchem ID :	12507071

Safety of [ 6812-16-4 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301+H311+H331
Precautionary Statements:	P261-P280-P301+P310-P311
Class:	6.1
UN#:	3439
Packing Group:	Ⅲ

Application In Synthesis of [ 6812-16-4 ]

* 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 [ 6812-16-4 ]

[ 6812-16-4 ] Synthesis Path-Downstream 1~35

1
[ 917-64-6 ]
[ 6812-16-4 ]
[ 703-98-0 ]

References: [1]Justus Liebigs Annalen der Chemie,1959,vol. 570,p. 155,163.

2
[ 6812-16-4 ]
phenylmagnesium bromide [ No CAS ]
[ 65202-31-5 ]

References: [1]Justus Liebigs Annalen der Chemie,1950,vol. 570,p. 155,159.

3
[ 6812-16-4 ]
5-bromo-2-hydroxy-3-methoxy-benzonitrile [ No CAS ]

References: [1]Justus Liebigs Annalen der Chemie,1950,vol. 570,p. 155,159.

4
2-hydroxy-3-methoxy-benzaldehyde-(O-acetyl oxime ) [ No CAS ]
[ 540750-97-8 ]
[ 6812-16-4 ]

References: [1]Justus Liebigs Annalen der Chemie,1950,vol. 570,p. 155,159.

5
2-hydroxy-3-methoxy-benzaldehyde-(O-acetyl oxime ) [ No CAS ]
[ 6812-16-4 ]

References: [1]Justus Liebigs Annalen der Chemie,1950,vol. 570,p. 155,159.

6
2-acetoxy-3-methoxy-benzaldehyde-(O-acetyl oxime ) [ No CAS ]
[ 6812-16-4 ]

References: [1]Journal of the Chemical Society,1934,p. 1651.

7
2-acetoxy-3-methoxy-benzaldehyde-(O-acetyl oxime ) [ No CAS ]
[ 108-24-7 ]
[ 6812-16-4 ]

References: [1]Journal of the Chemical Society,1934,p. 1651.

8
[ 6812-16-4 ]
[ 75-36-5 ]
[ 125629-15-4 ]

References: [1]Justus Liebigs Annalen der Chemie,1950,vol. 570,p. 155,159.

9
[ 2169-99-5 ]
[ 6812-16-4 ]

Yield	Reaction Conditions	Operation in experiment
97%	With iron(III) chloride; silica gel; In neat (no solvent); at 110℃; for 2.0h;Green chemistry;	General procedure: Aldoxime (1.0 mmol) and anhydrous FeCl3 (1.0 mmol) were intimately mixed with silica gel 60-120 mesh (1.0 g) in mortar and pestle. The resulting solid mixture was poured into a round-bottom flask (50 ml) and allowed to stir on magnetic stirrer at 110 C for an appropriate time (Table 2). The progress of the reaction was monitored by thin-layer chromatography (TLC). After completion of the reaction, the reaction mixture was extracted with ethyl acetate (3 15 ml) and washed several times with water. The combined organic mixture was dried over anhydrous Na2SO4, concentrated, and purified by column chromatography on silica gel 60-120 mesh using petroleum ether/ethyl acetate as eluent to afford pure nitrile.
4.55 g	In dimethyl sulfoxide; at 100℃; for 6.0h;	General procedure: Salicylaldehyde 1A (28.86g, 1 equiv.) was dissolved in DMSO (200ml) to give an orange solution. Hydroxylamine hydrochloride (29.31g, 2.2 equiv.) was charged and stirred at RT for 20 min to give a yellow solution, this was heated to 100 C for 6 hrs before being allowed to cool. Reaction was quenched into water (300ml) and extracted with diethyl ether (5x 100ml). Combined organic was washed with brine (2x 50ml), dried (Mg2SO4) and stripped to give a foul smelling red-brown solid (30.53g). Semi-pure material suitable for subsequent reactions was obtained by extraction of impurities into refluxing heptane (100ml) followed by cooling and tituation. Pure material for characterisation was obtained by flash chromatography (product adhered to silica, eluting with 1:9 EtOAc in hexane, Rf = 0.32) which yielded the title compound as a orange-red solid (20.58g, 73%)

References: [1]Synthetic Communications,2016,vol. 46,p. 685 - 691.
[2]Journal of the Chemical Society. Perkin transactions I,1983,p. 2973 - 2978.
[3]Tetrahedron Letters,2011,vol. 52,p. 5120 - 5123.

10
[ 148-53-8 ]
[ 6812-16-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With iron(III) chloride; hydroxylamine hydrochloride; In N,N-dimethyl-formamide; for 3.0h;Reflux;	General procedure: Aldehyde(1 mmol) and hydroxylamine hydrochloride (1.2 mmol) were added successively toa solution of anhydrous ferric chloride (0.5 mmol) in 5 ml dry DMF. The mixturewas reflux for appropriate time (Table 2). The progress of the reaction wasmonitored by TLC. After completion of the reaction, the solution was pouredinto 100 ml water and extract with ethyl acetate washed several times withwater. The combined organic mixture was dried over anhydrous Na2SO4,concentrated and the residue was purified by column chromatography on silicagel 60-120 mesh using petroleum ether/ethyl acetate (96:4) as eluent to affordthe pure nitrile. All the products were characterized by IR, 1H NMRand 13C NMR.
94%	With hydroxylamine hydrochloride; In N,N-dimethyl-formamide; for 1.0h;Reflux;	General procedure: Aldehyde (0.5 mmol) and hydroxylamine hydrochloride (0.75 mmol) were added successively to a solution of Fe3O4-CTAB NPs (5.7 mg) i.e Fe3O4 (1.8 mol%) in 5 ml dry DMF. The mixture was refluxed for appropriate time (table 3). The progress of the reaction was monitored by TLC. After completion of the reaction, the solution was poured into 100 ml water and extract with ethyl acetate, washed several times with water. The combined organic mixture was dried over anhydrous Na2SO4, concentrated and the residue was purified by column chromatography on silica gel 60-120 mesh using petroleum ether/ethyl acetate (95:5) as eluent to afford the pure nitrile. All the products were characterized by IR, 1H NMR and 13C NMR.
88%	With sodium azide; silica gel; toluene-4-sulfonic acid; at 120℃; for 3.0h;Green chemistry;	General procedure: Aldehyde (1 mmol) , sodium azide (2 mmol) and p-toluene sulphonic acid (3 mmole) were finely mixed with silica gel 60-120 mesh (1g) in mortar and pestle. The resultant solid mixture was poured into a round-bottom flask (50ml) and allowed to stir on magnetic stirrer at 120 for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the solution was poured into 100 ml water and extract with ethyl acetate, washed several times with water. The combined organic mixture was dried over anhydrous Na2SO4, concentrated and the residue was purified by column chromatography on silica gel 60-120 mesh using petroleum ether/ethyl acetate as eluent to afford the pure nitrile. All the products were characterized by IR, 1H NMR and 13C NMR.

4816 g (77%)

With hydroxylamine hydrochloride; sodium formate; In P2O5; formic acid; water;

Example 1 2-Hydroxy-3-methoxy-benzonitrile A suspension of 6375 g (41.94 mol) of o-vanillin, 3823 g (55 mol) of hydroxylamine hydrochloride and 6375 g (93.75 mol) of sodium formate in 14 l of formic acid was heated to about 90 to 95 C. with stirring. Increased evolution of gas and exothermic reaction commenced in this temperature range (heating was turned off). the exothermic reaction lasted for about 10 to 15 minutes (temperature rise to about 115 C.). The mixture was then stirred under reflux for a further 45 minutes. After completion of the reaction, the mixture was cooled to about +6 C. and stirred into a mixture of 6 kg of ice and 25 l of water. After 1 h, the solid was filtered off with suction and washed with about 12 l of water. It was then dried for 24 h at room temperature in a fresh air drying oven and for 120 h over P2O5 in a vacuum drying oven (room temperature). Yield: 4816 g (77%) of crystals, m.p. 54 C., Rf: 0.34 (toluene-ethyl acetate 3:1)

References: [1]Tetrahedron Letters,2013,vol. 54,p. 4885 - 4887.
[2]Journal of Organic Chemistry,2012,vol. 77,p. 5364 - 5370.
[3]Tetrahedron Letters,2016,vol. 57,p. 3618 - 3621.
[4]Tetrahedron Letters,2017,vol. 58,p. 2298 - 2301.
[5]Journal of the Chemical Society. Perkin transactions I,1983,p. 2973 - 2978.
[6]Collection of Czechoslovak Chemical Communications,2000,vol. 65,p. 280 - 296.
[7]Journal of Medicinal Chemistry,1999,vol. 42,p. 95 - 108.
[8]Phytochemistry,1988,vol. 27,p. 1483 - 1486.
[9]Patent: US2002/177616,2002,A1 .
[10]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 8419 - 8426.
[11]Tetrahedron Letters,2011,vol. 52,p. 5120 - 5123.

11
[ 6812-16-4 ]
[ 16420-13-6 ]
[ 88791-22-4 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1983,p. 2973 - 2978.

12
[ 6812-16-4 ]
[ 77-78-1 ]
[ 5653-62-3 ]

References: [1]Phytochemistry,1988,vol. 27,p. 1483 - 1486.

13
[ 921-01-7 ]
[ 6812-16-4 ]
(S)-2-(2-Hydroxy-3-methoxy-phenyl)-4,5-dihydro-thiazole-4-carboxylic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 95 - 108.

14
[ 6812-16-4 ]
[ 134563-11-4 ]
[ 269075-68-5 ]

References: [1]Collection of Czechoslovak Chemical Communications,2000,vol. 65,p. 280 - 296.

15
[ 6812-16-4 ]
[ 135-73-9 ]
[ 269075-67-4 ]

References: [1]Collection of Czechoslovak Chemical Communications,2000,vol. 65,p. 280 - 296.

16
[ 6812-16-4 ]
[ 70-11-1 ]
[ 269075-65-2 ]

References: [1]Collection of Czechoslovak Chemical Communications,2000,vol. 65,p. 280 - 296.

17
[ 6812-16-4 ]
[ 99-73-0 ]
3-Methoxy-2-[2-(4-bromophenyl)-2-oxoethoxy]benzonitrile [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,2000,vol. 65,p. 280 - 296.

18
[ 6812-16-4 ]
[ 78-95-5 ]
[ 916329-09-4 ]