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4-Chloro-2-pyridinamine

4-Chloro-2-pyridinamine structure

CAS No:
19798-80-2
Formula:
C5H5ClN2
Chemical Name:
4-Chloro-2-pyridinamine
Synonyms:
2-Pyridinamine,4-chloro-;Pyridine,2-amino-4-chloro-;4-Chloro-2-pyridinamine;2-Amino-4-chloropyridine;4-Chloro-2-aminopyridine;(4-Chloropyridin-2-yl)amine
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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Description

Light yellow Cryst

Compounds with a six membered aromatic ring containing NITROGEN. The saturated version is PIPERIDINES.

4-Chloro-2-pyridinamine Basic Attributes

Molecular Weight：

128.56

Exact Mass：

128.56

EC Number：

-0

DSSTox ID：

DTXSID70342444

HScode：

29333990

Characteristics

PSA：

38.9

XLogP3：

1.1

Appearance：

Colorless to yellow to brown Liquid

Density：

1.326±0.06 g/cm3(Predicted)

Melting Point：

130-131 °C

Boiling Point：

240.8±20.0 °C(Predicted)

Flash Point：

99.4±21.8 °C

Refractive Index：

1.607

Storage Conditions：

-20°C Freezer

Vapor Pressure：

0.0372mmHg at 25°C

Safety Information

Hazard category：

IRRITANT

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

22-36/37/38

safety instructions：

Marks：

Xi,Xn

Hazard note：

Irritant

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H302-H315-H319-H335

GHS Classification：

|Warning|H302 (93.18%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 44 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

Pyridines

4-Chloro-2-pyridinamine Use and Manufacturing

Synthesis of 4-Chloropyridin-2-amine (compound 65-2)[0000228] To a stirred solution of tert-butyl 4-chloropyridin-2-ylcarbamate (2 g, 8.7 mmol, 1 equiv) was addeda 4N solution of hydrogen chloride in dioxane (10 mL, 40 mmol, 4.6 equiv) . The solution was allowed to stir for 18 hours atroom temperature. The reaction was concentrated under reduced pressure to give compound 65-2 (HC1) as a reddish yellow solid (1.5 g, 100percent yield)Example 2.4: Preparation of 3-Hydroxy-8-morpholin-4-yl-4-oxo-4//-pyrido[l, 2- α]pyrimidine-2-carboxylic acid methyl ester; rt t-Butanol 2-Picolinic acid was reacted with thionyl chloride and methanol to provide methyl 4- chloro-2-picolinate which was hydrolysed and the hydrochloride salt and subjected to a Curtius rearrangement. Cleavage of the Boc protecting group afforded 2-amino-4- chloropyridine. The procedure described in W02006040520 was adapted to introduce the morpholine at position 4. This was cyclised to the intermediate ester using an adaptation of the procedure described in where the reaction was performed at 60° C.35 g of 4-chloropyridine-2-amide was added in portions to an aqueous calcium hypochlorite solution, and the aqueous calcium hypochlorite solution was 78 g.It is prepared by adding calcium hypochlorite and 1 liter of water. After heating up to 60-80 ° C, the reaction is carried out until the raw materials consume light, and the temperature is lowered to room temperature.Dichloromethane is extracted into the aqueous phase without product, the organic phase is dried over anhydrous sodium sulfate, and the solvent is removed.The ethanol was recrystallized to give a white solid, 30 g, yield 81percent.Example 3 Sodium hydroxide (39.6g, 990mmol) was dissolved in water (200mL) and cooled to 0–5°C. Bromine (10mL) was slowly dropped at 0°C and stirred for half hour. Then 4-chloropicolinamide (3) (13.47g, 86.3mmol) was added at 0°C and stirred for 5min. The reaction mixture was heated to 100°C and maintained at reflux to get a clear solution. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled to 0–5°C in 1h, filtered the precipitated solid, washed with chilled water, and dried at 50–55°C to give the corresponding crude product [27], which was purified by flash column chromatography (EtOAc : petroleum ether=1:1) to afford compound 4-chloropyridin-2-amine (4) as a white solid. Yield: 6.18g, 56percent. mp: 129–131°C. 1H NMR (DMSO-d6, ppm) δ: 7.93 (d, 1H, J=5.5Hz, CH), 7.74 (s, 2H, NH

Computed Properties

Molecular Weight:128.56
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:128.0141259
Monoisotopic Mass:128.0141259
Topological Polar Surface Area:38.9
Heavy Atom Count:8
Complexity:76.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Calcium chloride

Toluene

Tetrahydrofuran

Hexane

Potassium hydroxide

Sodium hydroxide

Ammonium hydroxide

Ethyl acetate

Sodium carbonate

Acetic acid

Acetone

Dimethylformamide

Sodium nitrite

Sodium bromide

Thionyl chloride

Nitrogen

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