231287-89-1|6-Bromo-4-nitropicolinic acid| Ambeed

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Quality Control of [ 231287-89-1 ] Purity: 97% SDS Specification

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Product Details of [ 231287-89-1 ]

CAS No. :	231287-89-1
Formula :	C₆H₃BrN₂O₄
M.W :	247.00
SMILES Code :	O=C(O)C1=NC(Br)=CC([N+]([O-])=O)=C1
MDL No. :	MFCD11046316
InChI Key :	YQBRMUXRAFVSPK-UHFFFAOYSA-N
Pubchem ID :	22176500

Safety of [ 231287-89-1 ]

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

Application In Synthesis of [ 231287-89-1 ]

* 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 [ 231287-89-1 ]

[ 231287-89-1 ] Synthesis Path-Downstream 1~9

1
2-bromo-6-methyl-4-nitro-pyridine [ No CAS ]
[ 231287-89-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With chromium(VI) oxide; sulfuric acid; at 0 - 70℃; for 4.5h;	To a solution of 2-bromo-6-methyl-4-nitro-pyridine (2.07 mmol) in concentrated H2SO4, Cr03 (8.28 mmol) was added at 0 C. The resulting solution was stirred at rt for 4 h. The mixture was then heated to 70 C for 30 min and then cooled to rt. Ice cold H20 (13 mL) was added slowly to afford a dark green heterogeneous solution. The mixture was allowed to stand at -20 C overnight. The crude product was filtered and recrystallized from H20 and MeOH to afford a white solid in 75% yield (385 mg): 'H NMR (DMSO-d6, 400 MHz) d 8.63 (d, J = 1.8 Hz, 1H, Ar H), 8.50 (d, J = 1.9 Hz, 1H, Ar H).
	With CrO3; In conc. sulphuric acid; ice-water;	EXAMPLE 69 4-(4-Aminobenzenesulphonyl)-6-bromopyridine-2-carbonitrile 0.44 g (0.002 mol) of 2-bromo-6-methyl-4-nitropyridine was dissolved in 2.2 ml of conc. sulphuric acid, treated with 0.84 g (0.0084 mol) of CrO3 and stirred at room temperature for 18 hrs. Then, the mixture was poured on to ice-water and the precipitate which thereby separated was filtered off under suction, washed with a large amount of water and dried in a high vacuum. There was obtained 0.35 g (70%) of 6-bromo-4-nitro-pyridine-2-carboxylic acid as beige crystals; m.p.: 172-173 C.
	With CrO3; In sulfuric acid; water;	a 6-Bromo-4-nitro-pyridine-2-carboxylic Acid To a solution of 2-bromo-6-methyl-4-nitro-pyridine (17.8 g, 82.0 mmol) (A. Puszko, Pr. Nauk. Akad. Ekon. im. Oskara Langego Wroclawiu, 1984, 278) 169) in conc. H2SO4 (100 ml) CrO3 (32.8 g, 328 mmol) was added maintaining T<55 C. After 4 hr the mixture was heated to 70 C. for 30 min and then cooled to rt. Ice-cold water (500 ml) was added maintaining T<70 C. The mixture was left overnight. The title compound crystallized as a beige material (76%). Mp. 173-175 C. (H2O), MS: m/e=246 (M+).

With CrO3; In sulfuric acid; water;

a 6-Bromo-4-nitro-pyridine-2-carboxylic acid To a solution of 2-bromo-6-methyl-4-nitro-pyridine (17.8 g, 82.0 mmol) (A. Puszko, Pr. Nauk. Akad. Ekon. im. Oskara Langego Wroclawiu, 1984, 278, 169) in conc. H2SO4 (100 ml) CrO3 (32.8 g, 328 mmol) was added maintaining T<55 C. After 4 hr the mixture was heated to 70 C. for 30 min and then cooled to rt. Ice-cold water (500 ml) was added maintaining T<70 C. The mixture was left overnight. The title compound crystallized as a beige material (76%). Mp. 173-175 C. (H2O), MS: m/e=246 (M+).

References: [1]Journal of Organic Chemistry,2020.
[2]Patent: WO2019/241787,2019,A1 .Location in patent: Page/Page column 97.
[3]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 829 - 832.
[4]Patent: US5990105,1999,A .
[5]Patent: US2003/119870,2003,A1 .
[6]Patent: US2003/144525,2003,A1 .

2
[ 231287-89-1 ]
(6-bromo-4-nitro-pyridin-2-yl)-methanol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 829 - 832.

3
[ 231287-89-1 ]
[ 521917-52-2 ]

Yield	Reaction Conditions	Operation in experiment
2.0 g (34%)	With borane; iron; acetic acid; In tetrahydrofuran;	b (4-Amino-6-bromo-pyridin-2-yl)-methanol A solution of 6-bromo-4-nitro-pyridine-2-carboxylic acid (example 6a) (6.60 g, 29.1 mmol) in THF (150 ml) was treated with borane/THF (87 ml of a 1M solution). The mixture was refluxed for 6 hr, then powdered iron (16.3 g, 291 mmol) was added, followed by acetic acid (150 ml). Reflux was maintained for 6 hr, the mixture was filtered, evaporated and partitioned (AcOEt/NaHCO3-solution). The organic phase was dried (Na2SO4), concentrated and chromatographed (SiO2 with CH2Cl2/MeOH=93/7) to provide 2.0 g (34%) of (4-amino-6-bromo-pyridin-2-yl)-methanol as a white solid material. Mp. 144-145 C. (AcOEt), MS: m/e=202 (M1).
2.0 g (34%)	With borane; iron; acetic acid; In tetrahydrofuran;	b (4-Amino-6-bromo-pyridin-2-yl)-methanol A solution of 6-bromo-4-nitro-pyridine-2-carboxylic acid (6.60 g, 29.1 mmol) in THF (150 ml) was treated with borane/THF (87 ml of a 1M solution). The mixture was refluxed for 6 hr, then powdered iron (16.3 g, 291 mmol) was added, followed by acetic acid (150 ml). Reflux was maintained for 6 hr, the mixture was filtered, evaporated and partitioned (AcOEt/aqueous NaHCO3-solution). The organic phase was dried (Na2SO4), concentrated and chromatographed (SiO2 with CH2Cl/MeOH=93/7) to provide 2.0 g (34%) of the title compound as a white solid material. Mp. 144-145 C. (AcOEt), MS: m/e=202 (M+).

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 829 - 832.
[2]Patent: US2003/119870,2003,A1 .
[3]Patent: US2003/144525,2003,A1 .

4
[ 231287-89-1 ]
[4-amino-6-(3,4-dihydro-1H-isoquinolin-2-yl)-pyridin-2-yl]-methanol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 829 - 832.
[2]Patent: US2003/119870,2003,A1 .

5
[ 1336-21-6 ]
[ 530-62-1 ]
[ 231287-89-1 ]
6-bromo-4-nitropyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide; water;	1.3 g (0.00526 mol) of 6-bromo-4-nitropyridine-2-carboxylic acid were dissolved in 10 ml of dimethylformamide, treated at 5 C. with 0.94 g (0.0058 mol) of 1,1-carbonyldiimidazole and subsequently stirred at room temperature for 3 hrs. Then, 40 ml of 25% NH4 OH in water was added thereto and the mixture was stirred at room temperature for 1 hr. The reaction mixture was partitioned in water and dichloromethane and the organic phase was washed with water and sat. sodium chloride solution, dried over MgSO4 and concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane 1:1. There were obtained 1.1 g (85%) of 6-bromo-4-nitropyridine-2-carboxamide as white crystals; m.p.: 179-180 C.

References: [1]Patent: US5990105,1999,A .

6
[ 231287-89-1 ]
[4-amino-6-(3,4-dihydro-naphthalen-2-yl)-pyridin-2-yl]-methanol [ No CAS ]

References: [1]Patent: US2003/144525,2003,A1 .

7
[ 231287-89-1 ]
methyl 6-((4-fluorophenyl)amino)-4-nitropicolinate [ No CAS ]

References: [1]Patent: WO2019/241787,2019,A1 .
[2]Journal of Organic Chemistry,2020.

8
[ 231287-89-1 ]
methyl 4-amino-6-((4-fluorophenyl)amino)picolinate [ No CAS ]

References: [1]Journal of Organic Chemistry,2020.
[2]Patent: WO2019/241787,2019,A1 .

9
[ 67-56-1 ]
[ 231287-89-1 ]
methyl 6-bromo-4-nitropicolinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With sulfuric acid;pH 4.0;Reflux;	<strong>[231287-89-1]6-bromo-4-nitropicolinic acid</strong> (1.21 mmol) was dissolved in anhydrous methanol followed by the addition of concentrated H2S04 (0.301 mmol). The mixture was heated at reflux overnight. The reaction was monitored using TLC (100% CH2CI2). After completion, the reaction was cooled to rt and the pH was adjusted to pH = 4. The mixture was concentrated by rotary evaporation and the resulting residue was dissolved in EtOAc. The organic mixture was washed with water. The aqueous layer was extracted with EtOAc (3X), dried with Na2OS4, filtered, and concentrated by rotary evaporation to afford a white solid (289 mg) in 91% yield. The solid was used without further purification: 1H NMR (Methanol-d4, 400 MHz) d 8.69 (d, J = 1.8 Hz, 1H, Artf), 8.6 (d, J = 1.8 Hz, 1H, Artf), 4.03 (s, 3 H, OG ); HRMS (ESI+) calcd for C13H11FN3O4 [M+H]+, m/z = 292.0729, found 292.0734.

References: [1]Journal of Organic Chemistry,2020.
[2]Patent: WO2019/241787,2019,A1 .Location in patent: Page/Page column 97-98.

Historical Records

Technical Information

• Alkyl Halide Occurrence • Arndt-Eistert Homologation • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hunsdiecker-Borodin Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Carboxylic Acids • Reactions of Dihalides • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Ugi Reaction

Related Functional Groups of
[ 231287-89-1 ]

Bromides

A534178 [1211533-23-1]

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Carboxylic Acids

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Nitroes

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Related Parent Nucleus of
[ 231287-89-1 ]

Pyridines

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CAS No.: 231287-89-1

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