5327-32-2|2-Acetamido-4-picoline| Ambeed

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Quality Control of [ 5327-32-2 ] Purity: 98% SDS Specification

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Product Details of [ 5327-32-2 ]

CAS No. :	5327-32-2
Formula :	C₈H₁₀N₂O
M.W :	150.18
SMILES Code :	CC1=CC(NC(C)=O)=NC=C1
MDL No. :	MFCD00234432
InChI Key :	QGZHGSGLCZEGHA-UHFFFAOYSA-N
Pubchem ID :	220485

Safety of [ 5327-32-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H319
Precautionary Statements:	P264-P270-P280-P301+P312-P305+P351+P338-P330-P337+P313

Application In Synthesis of [ 5327-32-2 ]

* 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.

Downstream synthetic route of [ 5327-32-2 ]

[ 5327-32-2 ] Synthesis Path-Downstream 1~3

1
[ 5327-32-2 ]
2-acetamido-4-methylpyridinium hydrobromide perbromide [ No CAS ]
[ 142404-82-8 ]

Yield	Reaction Conditions	Operation in experiment
88%; 83.1%	With bromine; In dichloromethane;	Into a 100 ml three-neck flask, 5.0 g (0.033 mol) of Ia was introduced. Then, 15 ml of dichloromethane was added thereto so as to dissolve Ia. Thereafter, 5.34 g (0.33 mol) of bromine was added dropwise thereto. An orange-colored slurry was formed. After being stirred overnight at room temperature, the slurry was filtered under reduced pressure. When the cake obtained by the filtration was dried, 5.5 g (yield: 88%) of IIIa was obtained. After the pH of the mother liquor after the filtration under reduced temperature was adjusted to 9-10 with 5% sodium hydroxide aqueous solution, an organic layer was separated therefrom. When the solvent was evaporated away, 3.14 g (yield: 83.1%) of IIa was obtained as a slightly brown crystal.
88%; 83.1%	With bromine; In dichloromethane;	Into a 100ml three-neck flask, 5.0g (0.033mol) of Ia was introduced. Then, 15ml of dichloromethane was added thereto so as to dissolve Ia. Thereafter, 5.34g (0.33mol) of bromine was added dropwise thereto. An orange-colored slurry was formed. After being stirred overnight at room temperature, the slurry was filtered under reduced pressure. When the cake obtained by the filtration was dried, 5.5g (yield: 88%) of IIIa was obtained. After the pH of the mother liquor after the filtration under reduced temperature was adjusted to 9-10 with 5% sodium hydroxide aqueous solution, an organic layer was separated therefrom. When the solvent was evaporated away, 3.14g (yield: 83.1%) of IIa was obtained as a slightly brown crystal.

References: [1]Patent: US5290943,1994,A .
[2]Patent: EP530524,1993,A1 .

2
[ 5327-32-2 ]
[ 142404-82-8 ]

Yield	Reaction Conditions	Operation in experiment
82%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0℃; for 0.5h;	(2); N-Bromosuccinimide (6.8 mmol, 1.2 g) was added to a N'N- dimethylformamide solution (20 ml) of 2-(acetylamino)-4-picoline (6.7 mmol, 1 g) at 0C, followed by stirring at the same temperature for 30 minutes. Water (20 ml) was added to the resulting reaction mixture on ice to stop the reaction, and an aqueous layer was extracted with diethyl ether five times. An organic layer was dried over anhydrous sodium sulfate, and filtered, followed by distilling away a solvent under reduced pressure. The resulting crude product was purified with column chromatography to obtain 1.25 g of 2-(acetylamino)-5-bromo-4-picoline (yield 82%). 1H NMR δ ppm (300 MHz, CDCl3) data of this compound are 8.27 (s, IH), 8.13 (s, IH), 7.85 (brs, IH), 2.41 (s, 3H), 2.20 (s, 3H).
	With bromine; In CH3 CO2 Na; water;	Example 9 Single step synthesis of 2-acetamido-4-methyl-5-bromopyridine (IIa) by bromination of 2-acetamido-4-methylpyridine (Ia) in aqueous solution of sodium acetate (CH3 CO2 Na) Into a 300 ml three-neck flask, 155 ml of water was introduced and then a solution in which 12.3 g (0.15 mol) of CH3 CO2 Na has been dissolved in 25 ml of water was added thereto. The pH at this moment was 8.8. Then, 9.0 g (0.06 mol) of 2-acetamido-4-methylpyridine (Ia) was added thereto and dispersed therein. Thereafter, 9.6 g (0.06 mol) of bromine was added dropwise thereto for 12 minutes at 19-24 C. After being stirred overnight, the mixture was filtered under reduced pressure. The cake obtained by the filtration was washed with water.

References: [1]Patent: WO2009/88103,2009,A1 .Location in patent: Page/Page column 15.
[2]Patent: US5290943,1994,A .
[3]Organic Process Research and Development,2017,vol. 21,p. 1095 - 1109.

3
2-acetamido-4-methylpyridinium hydrobromide perbromide [ No CAS ]
[ 142404-82-8 ]
[ 5327-32-2 ]

Yield	Reaction Conditions	Operation in experiment
	In water;	While being stirred at room temperature, 97.1g of the above-obtained mixture of IIa and IIIa was added thereto. After being heated on a hot water bath and reacted for two hours at 38C, the reaction mixture was further reacted overnight at room temperature and then reacted for two hours on a hot bath at 45C. The color of the slurry gradually changed from orange to yellow. After being cooled to room temperature, the pH of the slurry was adjusted to 4.96 with 5% NaOH aqueous solution. Then, it was filtered under reduced pressure. The cake obtained by the filtration was washed with 40ml of water. When the washed cake was dried, 62.4g of IIa was obtained as pale brown powder.

References: [1]Patent: EP530524,1993,A1 .

Historical Records

Technical Information

• Acyl Group Substitution • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Hydride Reductions • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Related Functional Groups of
[ 5327-32-2 ]

Amides

A731393 [1367908-69-7]

N-(4-(Aminomethyl)pyridin-2-yl)acetamide

Similarity: 0.96

A731393 [1367908-69-7]

N-(4-(Aminomethyl)pyridin-2-yl)acetamide

Similarity: 0.96

A238157 [1445876-40-3]

N-(4-Ethynylpyridin-2-yl)acetamide

Similarity: 0.93

A731393 [1367908-69-7]

N-(4-(Aminomethyl)pyridin-2-yl)acetamide

Similarity: 0.96

A238157 [1445876-40-3]

N-(4-Ethynylpyridin-2-yl)acetamide

Similarity: 0.93

Amines

A731393 [1367908-69-7]

N-(4-(Aminomethyl)pyridin-2-yl)acetamide

Similarity: 0.96

A731393 [1367908-69-7]

N-(4-(Aminomethyl)pyridin-2-yl)acetamide

Similarity: 0.96

A238157 [1445876-40-3]

N-(4-Ethynylpyridin-2-yl)acetamide

Similarity: 0.93

A731393 [1367908-69-7]

N-(4-(Aminomethyl)pyridin-2-yl)acetamide

Similarity: 0.96

A238157 [1445876-40-3]

N-(4-Ethynylpyridin-2-yl)acetamide

Similarity: 0.93

Related Parent Nucleus of
[ 5327-32-2 ]

Pyridines

A731393 [1367908-69-7]

N-(4-(Aminomethyl)pyridin-2-yl)acetamide

Similarity: 0.96

A731393 [1367908-69-7]

N-(4-(Aminomethyl)pyridin-2-yl)acetamide

Similarity: 0.96

A238157 [1445876-40-3]

N-(4-Ethynylpyridin-2-yl)acetamide

Similarity: 0.93

A731393 [1367908-69-7]

N-(4-(Aminomethyl)pyridin-2-yl)acetamide

Similarity: 0.96

A238157 [1445876-40-3]

N-(4-Ethynylpyridin-2-yl)acetamide

Similarity: 0.93

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CAS No.: 5327-32-2

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