14432-16-7

Usage

Chemical Properties

light yellow solid

InChI:InChI=1/C5H4ClN2O3/c6-5-3-4(8(10)11)1-2-7(5)9/h1-3,5H/q+1

Synthetic route

2-chloropyridine-N-oxide (2402-95-1) → 2-chloro-4-nitropyridine-N-oxide (14432-16-7)

Conditions	Yield
nitration;	93%
With sulfuric acid; nitric acid at 90℃; for 4h;	78%
With sulfuric acid; nitric acid for 2h; Nitration;	72%

2-chloro-4-nitropyridine (23056-36-2) → 2-chloro-4-nitropyridine-N-oxide (14432-16-7)

Conditions	Yield
Stage #1: 2-chloro-4-nitropyridine With urea hydrogen peroxide adduct; trifluoroacetic acid In dichloromethane at 0 - 20℃; for 72h; Stage #2: With sodium dithionite In dichloromethane; water for 0.25h; Stage #3: With hydrogenchloride In dichloromethane; water	90%
With urea hydrogen peroxide adduct; trifluoroacetic anhydride In dichloromethane at 0 - 20℃; for 4.5h;	84%

2-chloropyridine N-oxide hydrochloride (20295-64-1) → 2-chloro-4-nitropyridine-N-oxide (14432-16-7)

Conditions	Yield
With sulfuric acid; nitric acid at 90 - 100℃; for 2.5h;	82.5%
With sodium hydroxide; nitric acid In sulfuric acid	37%
With sulfuric acid; nitric acid In (2S)-N-methyl-1-phenylpropan-2-amine hydrate
With sulfuric acid; nitric acid In (2S)-N-methyl-1-phenylpropan-2-amine hydrate

2-chloropyridine (109-09-1) → 2-chloro-4-nitropyridine-N-oxide (14432-16-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / aq. H2O2 / trifluoroacetic acid / 4 h 2: 72 percent / aq. HNO3, H2SO4 / 2 h View Scheme
Multi-step reaction with 2 steps 1: 30percent aq. H2O2, AcOH / 48 h / 60 °C 2: HNO3, conc. H2SO4 / 2.5 h / 90 °C View Scheme
Multi-step reaction with 2 steps 1: H2O2 / acetic anhydride 2: HNO3, H2SO4 View Scheme

2-aminopyridine N-oxide (14150-95-9) → 2-chloro-4-nitropyridine-N-oxide (14432-16-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: concentrated sulfuric acid; peroxomonosulfuric acid 3: concentrated sulfuric acid; nitric acid View Scheme

4-carboxy-2-nitropyridine N-oxide (2403-02-3) → 2-chloro-4-nitropyridine-N-oxide (14432-16-7)

Conditions	Yield
Multi-step reaction with 2 steps 2: concentrated sulfuric acid; nitric acid View Scheme

2-chloropyridine-N-oxide (2402-95-1) → 2-chloro-4-nitropyridine-N-oxide (14432-16-7) + 2-Chloro-4-nitropyidine-N oxide

Conditions	Yield
With sulfuric acid; nitric acid

2-chloro-4-nitropyridine-N-oxide (14432-16-7) + 1-amino-propan-2-ol → 1-(4-nitro-1-oxy-pyridin-2-ylamino)-propan-2-ol

Conditions	Yield
In ethanol at 80℃; for 13h;	99%

2-chloro-4-nitropyridine-N-oxide (14432-16-7) → 4-Amino-2-chloropyridine (14432-12-3)

Conditions	Yield
With hydrogenchloride; iron In ethanol for 3h; Reduction; Heating;	95%
With hydrogen; Ra-Ni In methanol	90%
With hydrogenchloride; iron In ethanol; water Reflux;	85%

2-chloro-4-nitropyridine-N-oxide (14432-16-7) → 2,4-dichloropyridine 1-oxide (13602-59-0)

Conditions	Yield
With acetyl chloride at 70 - 75℃; for 0.416667h;	94%
With acetyl chloride for 0.666667h;	80%

2-chloro-4-nitropyridine-N-oxide (14432-16-7) + sodium methylate (124-41-4) → 2-chloro-4-methoxypyridine N-oxide (38608-87-6)

Conditions	Yield
With sulfuric acid; nitric acid In methanol at 20℃; for 48h;	94%
In methanol

2-chloro-4-nitropyridine-N-oxide (14432-16-7) + dimethyl amine (124-40-3) → 2-(dimethylamino)-4-nitropyridine 1-oxide (36100-42-2)

Conditions	Yield
In tetrahydrofuran; ethanol at 90℃; for 5h;	91%
In water at 100℃; Inert atmosphere; Sealed tube;

(S)-N-(2,6-diisopropyl-phenyl)pyrrolidine-2-carboxamide (943784-90-5) + 2-chloro-4-nitropyridine-N-oxide (14432-16-7) → (S)-2-(2-((2,6-diisopropylphenyl)carbamoyl)pyrrolidin-1-yl)-4-nitropyridine 1-oxide

Conditions	Yield
With triethylamine In tetrahydrofuran at 70℃; for 10h;	90%

2-chloro-4-nitropyridine-N-oxide (14432-16-7) → 2-chloro-4-nitropyridine (23056-36-2)

Conditions	Yield
With phosphorus trichloride In dichloromethaneu for 4h; Reflux;	88%
With phosphorus trichloride In chloroform at 20℃; Heating / reflux;	78%
With ethyl acetate; phosphorus trichloride

2-chloro-4-nitropyridine-N-oxide (14432-16-7) + (2S)-N-benzhydrylpyrrolidine-2-carboxamide (748149-61-3) → (S)-2-(2-(benzhydrylcarbamoyl)pyrrolidin-1-yl)-4-nitropyridine 1-oxide

Conditions	Yield
With triethylamine In tetrahydrofuran at 70℃; for 10h;	88%

2-chloro-4-nitropyridine-N-oxide (14432-16-7) + histamine (51-45-6) → 4-{[2-(1H-Imidazol-4-yl)ethyl]amino}-2-chloropyridine + [2-(1H-Imidazol-4-yl)-ethyl]-(5-nitro-1-oxy-pyridin-2-yl)-amine

Conditions	Yield
With potassium hydrogencarbonate In isopropyl alcohol at 21℃; for 72h;	A 87% B n/a
With potassium hydrogencarbonate In isopropyl alcohol at 21℃; for 72h;

2-chloro-4-nitropyridine-N-oxide (14432-16-7) + ethyl spiro[indole-3,4'-piperidine]-1(2H)-dicarboxylate (937255-13-5) → ethyl 1'-(4-nitro-1-oxidopyridin-2-yl)spiro[indole-3,4'-piperidine]-1(2H)-dicarboxylate (937255-16-8)

Conditions	Yield
With triethylamine In tert-Amyl alcohol at 50℃;	87%

2-chloro-4-nitropyridine-N-oxide (14432-16-7) + 1-thiopropane (107-03-9) → 2-chloro-4-(propylsulfanyl)pyridine-N-oxide (1186127-82-1) + 4-nitro-2-(propylsulfanyl)pyridine-N-oxide (1186127-84-3)

Conditions	Yield
With sodium acetate In ethanol at 50℃;	A 86% B 10%

2-chloro-4-nitropyridine-N-oxide (14432-16-7) + (2S)-N-phenylpyrrolidine-2-carboxamide (25746-83-2, 64030-43-9, 104261-87-2) → (S)-4-nitro-2-(2-(phenylcarbamoyl)pyrrolidin-1-yl)pyridine 1-oxide

Conditions	Yield
With triethylamine In tetrahydrofuran at 70℃; for 10h;	86%

(S)-N-(2,6-diethylphenyl)pyrrolidine-2-carboxamide + 2-chloro-4-nitropyridine-N-oxide (14432-16-7) → (S)-2-(2-((2,6-diethylphenyl)carbamoyl)pyrrolidin-1-yl)-4-nitropyridine 1-oxide

Conditions	Yield
With triethylamine In tetrahydrofuran at 70℃; for 10h;	85%

2-chloro-4-nitropyridine-N-oxide (14432-16-7) + L-proline tert-butylamide (128018-18-8) → (S)-2-(2-(tert-butylcarbamoyl)pyrrolidin-1-yl)-4-nitropyridine 1-oxide

Conditions	Yield
With triethylamine In tetrahydrofuran at 70℃; for 10h;	82%

2-chloro-4-nitropyridine-N-oxide (14432-16-7) + methyl spiro[indole-3,4'-piperidine]-1(2H)-dicarboxylate (937255-12-4) → methyl 1'-(4-nitro-1-oxidopyridin-2-yl)spiro[indole-3,4'-piperidine]-1(2H)-dicarboxylate (937255-15-7)

Conditions	Yield
With triethylamine In tert-Amyl alcohol at 50℃;	79%

2-chloro-4-nitropyridine-N-oxide (14432-16-7) + (S)-N-(3,5-bis(trifluoromethyl)phenyl)pyrrolidine-2-carboxamide (875542-94-2) → (S)-2-(2-((3,5-bis(trifluoromethyl)phenyl)carbamoyl)pyrrolidin-1-yl)-4-nitropyridine 1-oxide

Conditions	Yield
With triethylamine In tetrahydrofuran at 70℃; for 10h;	78%

2-chloro-4-nitropyridine-N-oxide (14432-16-7) + cyclohexylamine (108-91-8) → cyclohexyl-(4-nitro-1-oxy-pyridin-2-yl)-amine (75291-50-8)

Conditions	Yield
In ethanol at 80℃; for 13h;	76%

2-chloro-4-nitropyridine-N-oxide (14432-16-7) + isopropyl spiro[indole-3,4'-piperidine]-1(2H)-dicarboxylate (937255-14-6) → isopropyl 1'-(4-nitro-1-oxidopyridin-2-yl)spiro[indole-3,4'-piperidine]-1(2H)-dicarboxylate (937255-17-9)

Conditions	Yield
With triethylamine In tert-Amyl alcohol at 50℃;	75%

2-chloro-4-nitropyridine-N-oxide (14432-16-7) + 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one (291509-79-0) → 7-methoxy-3-(4'-nitro-1'-oxy-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-1.3.4,5-tetrahydro-benzo[d][1,3]diazepin-2-one (1231750-46-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 2h;	75%

2-chloro-4-nitropyridine-N-oxide (14432-16-7) + methylamine (74-89-5) → 2-methylamino-4-nitropyridine N-oxide (75291-48-4)

Conditions	Yield
	74%

methanol (67-56-1) + 2-chloro-4-nitropyridine-N-oxide (14432-16-7) → 2-chloro-4-methoxypyridine N-oxide (38608-87-6)

Conditions	Yield
With sodium hydride at 0℃; for 0.5h;	70%

methanol (67-56-1) + 2-chloro-4-nitropyridine-N-oxide (14432-16-7) → 2,4-dimethoxypyridine N-oxide (6890-63-7)

Conditions	Yield
With sodium for 1h; Heating;	70%

2-chloro-4-nitropyridine-N-oxide (14432-16-7) → 2,6-dichloro-4-nitro-pyridine (25194-01-8)

Conditions	Yield
With trichlorophosphate at 110℃; for 2.5h;	70%

2-chloro-4-nitropyridine-N-oxide (14432-16-7) + 2,3-dihydrospiro[indene-1,4-piperidine]-3-amine (937254-70-1) → 1'-(4-nitro-1-oxidopyridin-2-yl)-2,3-dihydrospiro[indene-1,4'-piperidin]-3-amine (937254-71-2)

Conditions	Yield
Stage #1: 2,3-dihydrospiro[indene-1,4-piperidine]-3-amine With sodium carbonate In 4-methyl-2-pentanone at 110℃; for 3h; Stage #2: 2-chloro-4-nitropyridine-N-oxide In 4-methyl-2-pentanone at 80℃;	70%

2-chloro-4-nitropyridine-N-oxide (14432-16-7) + (S)-N-methyl-N-phenyl-pyrrolidine-2-carboxamide (1173169-85-1) → (S)-2-(2-(methyl(phenyl)carbamoyl)pyrrolidin-1-yl)-4-nitropyridine 1-oxide

Conditions	Yield
With triethylamine In tetrahydrofuran at 70℃; for 10h;	70%

2-chloro-4-nitropyridine-N-oxide (14432-16-7) + tert-butyl 3-aminopiperidine-1-carboxylate → 3-(4-nitro-1-oxy-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

Conditions	Yield
In ethanol at 80℃; for 13h;	67%

morpholine (110-91-8) + 2-chloro-4-nitropyridine-N-oxide (14432-16-7) → 2-(N-morpholinyl)-4-nitropyridine N-oxide (35981-62-5)

Conditions	Yield
In ethanol at 20℃; for 3h;	63%
In ethanol

Upstream product

• 2402-95-1 2-chloropyridine-N-oxide 
• 14150-95-9 2-aminopyridine N-oxide 
• 2403-02-3 4-carboxy-2-nitropyridine N-oxide 
• 20295-64-1 2-chloropyridine N-oxide hydrochloride 
• 23056-36-2 2-chloro-4-nitropyridine 
• 109-09-1 2-chloropyridine 

Downstream Products

• 14432-12-3 4-Amino-2-chloropyridine 
• 23056-36-2 2-chloro-4-nitropyridine 
• 129836-41-5 2-allyloxy-4-nitropyridine N-oxide 
• 129836-50-6 2-benzyloxy-4-nitropyridine N-oxide 
• 13602-59-0 2,4-dichloropyridine-N-oxide 
• 52092-45-2 2-amino-4-nitropyridine N-oxide 
• 117535-03-2 6-chloro-3-cyano-2-phenylfuro<3,2-c>pyridine 
• 19404-40-1 2-Methylamino-3,5-dinitropyridin 
• 129836-51-7 N-benzyloxy-4-nitro-2-pyridone 
• 26452-80-2 2,4-dichloropyridine 
• 73583-37-6 2-chloro-4-bromopyridine 
• 153034-86-7 2-chloro-4-iodopyridine 
• 33252-30-1 2-chloro-4-pyridinenitrile 
• 6313-54-8 2-chloroisonicotinic acid, 

Relevant academic research and scientific papers

Preparation method of 2-chloro-4-aminopyridine

The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of 2-chloro-4-aminopyridine. The preparation method comprises the following steps: (1) using 2-chloropyridine as a raw material and chloroform as a solvent, and generating 2-chloropyridine oxide under the action of m-chloroperoxybenzoic acid; (2) reacting 2-chloropyridine oxide with a mixed acid composed of concentrated nitric acid and concentrated sulfuric acid to generate 2-chloro-4-nitropyridine oxynitride; and (3) reducing 2-chloro-4-nitropyridine oxynitride into 2-chloro-4-aminopyridine. The method has the beneficial effects that the reaction conditions are mild, the operation is easy, the post-treatment is simple, the scale-up production is easy, the method is very suitable for industrial production; the catalytic effect is good, the yield is high; the raw materials are cheap, and the production cost is low.

A 2 - chloro -4 - aminopyridine preparation method

The invention belongs to the field of organic synthesis, in particular relates to a 2 - chloro - 4 - aminopyridine preparation method, comprises the following steps: (1) to 2 - chloro pyridine as raw materials, chloroform as solvent, under the action of the meta-chloroperoxybenzoic acid to produce 2 - chloro pyridine oxide; (2) 2 - chloro pyridine oxide by the concentrated nitric acid in concentrated sulfuric acid the acid produced by the reaction of a 2 - chloro - 4 - nitro pyridine nitrogen oxides; (3) 2 - chloro - 4 - nitro pyridine nitrogen oxide reduction is 2 - chloro - 4 - aminopyridine. The beneficial effect of the invention is: mild reaction conditions, is easy to operate, after treatment is simple, and easy to enlarge production, is extremely suitable for industrial production; good catalytic effect, high yield; low prices of raw materials, the production cost is low.

9H-PYRROLO-DIPYRIDINE DERIVATIVES

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Design and synthesis of purine analogues as highly specific ligands for FcyB, a ubiquitous fungal nucleobase transporter

In the course of our study on fungal purine transporters, a number of new 3-deazapurine analogues have been rationally designed, based on the interaction of purine substrates with the Aspergillus nidulans FcyB carrier, and synthesized following an effective synthetic procedure. Certain derivatives have been found to specifically inhibit FcyB-mediated [3H]-adenine uptake. Molecular simulations have been performed, suggesting that all active compounds interact with FcyB through the formation of hydrogen bonds with Asn163, while the insertion of hydrophobic fragments at position 9 and N6 of 3-deazaadenine enhanced the inhibition.

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