Home Cart Sign in  
Chemical Structure| 6313-55-9 Chemical Structure| 6313-55-9

Structure of 6313-55-9

Chemical Structure| 6313-55-9

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 6313-55-9 ]

CAS No. :6313-55-9
Formula : C6H5ClN2O2
M.W : 172.57
SMILES Code : O=C(O)C1=CC(Cl)=NC(N)=C1
MDL No. :MFCD11036352
InChI Key :XELVYABXHBMJRZ-UHFFFAOYSA-N
Pubchem ID :236986

Safety of [ 6313-55-9 ]

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

Application In Synthesis of [ 6313-55-9 ]

* 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 [ 6313-55-9 ]

[ 6313-55-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 67-56-1 ]
  • [ 6313-55-9 ]
  • [ 1005508-80-4 ]
YieldReaction ConditionsOperation in experiment
71% Compound 24. El CI gas was passed through a solution o i -ani i no-6-ch loropyri dine -4- carboxylic acid2 in methanol (50.0 mL) until saturation and the reaction mixture was stirred for 12 h. Methanol ic solution was concentrated and the solid obtained was neutralized with a solution of sodium bicarbonate. The mixture was extracted with ethyl acetate, washed with water and dried (Na2S04). Ethyl acetate solution was concentrated to the methyl ester 14 as light brown solid. Yield 2.1 g (71 %). MS: 187.1 (M+H)+
  • 2
  • [ 1005508-80-4 ]
  • [ 6313-55-9 ]
YieldReaction ConditionsOperation in experiment
2.2 g With water; sodium hydroxide; In tetrahydrofuran; at 0 - 25℃; for 3h; Trimethylsilyl)diazomethane (8.7 mL, 17.5 mmol) was added dropwise to a solution of 2-chloro- 6-[(2,4-dimethoxyphenyl)methylamino]pyridine-4-carboxylic acid (4.7 g, 14.56 mmol) in methanol (5 mL) and dichloromethane (15 mL) at 0C and stirred 25 minutes at 25C. The solution was concentrated resulting in methyl 2-chloro-6-[(2,4- dimethoxyphenyl)methylamino]pyridine-4-carboxylate (5.0g) as a yellow solid which was used as such. TFA (5 mL) was added to a solution of methyl 2-chloro-6-[(2,4- dimethoxyphenyl)methylamino]pyridine-4-carboxylate (5.0g, 14.9 mmol) in dichloromethane (20 mL) and stirred 30 minutes at 25C. The reaction mixture was concentrated. The resulting solid was triturated 30 minutes in methyl tert-butyl ether (40 mL). The solids were filtered off and washed with methyl tert-butyl ether (10 mL) resulting in methyl 2-amino-6-chloro-pyridine- 4-carboxylate (3.0 g) as a light yellow solid. Sodium hydroxide (3.0g, 75.0 mmol) was added to a solution of methyl 2-amino-6-chloro-pyridine-4-carboxylate (2.8 g, 15 mmol) in water (10 mL) and THF (40 mL) at 0C and stirred 3 hours at 25C. The reaction mixture was cooled to 0C and acidified with HC1 (7 mL). The brown solid was filtered off, washed with water (30 mL) and THF (10 mL) and was lyophilized, resulting in 2-amino-6-chloro-pyridine-4-carboxylic acid (2.2g). 1H NMR (400MHz, DMSO-d6) δ = 6.87 (s, 1H), 6.80 (s, 1H), 6.71 (br. s., 2H). 2-amino- 6-chloro-pyridine-4-carboxylic acid (1.2g, 6.95 mmol) was dissolved in toluene (10 mL). Then triethylamine (2.97 g, 8.35 mmol), benzyl alcohol (3.01g, 27.82 mmol) and diphenylphosphoryl azide (2.97g, 8.35 mmol) were added and heated at 110C during 16 hours. The reaction mixture was cooled. EtOAc (100 mL) was added and washed with NaHC03 (sat.aq. 60 mL). The mixture was filtered and the solids washed with EtOAc (30 mL) the organic layer was separated from the filtrate. The water layer was extracted with EtOAc (3 x 30mL) The organic layers were combined and washed with brine (70 mL), dried over Na2S04, filtered and concentrated under reduce pressure resulting in a brown oil. The oil was purified by column chromatography (Si02, Petroleum ether/Ethyl acetate=0 to 50% resulting in benzyl N-(2-amino-6-chloro-4- pyridyl)carbamate as a colorless oil. Sodium nitrite (894 mg, 12.96 mmol) was added to a solution of benzyl N-(2-amino-6-chloro-4-pyridyl)carbamate (360 mg, 1.30 mmol) in pyridine hydrofluoride (1 mL) at 0C and stirred 2 hours at 25C. NaHC03 (100 mL sat.aq.) was added. The mixture was extracted with EtOAc (3 x 30 mL). The combined organic layers were washed with brine (70 mL), dried over Na2S04, filtered, and concentrated in vacuo. The obtained residue was purified by column chromatography (Si02, Ethyl acetate/Petroleum ether=0 to 30%, TLC pentane:EtOAc =3: 1, Rf=0.8) resulting in benzyl N-(2-chloro-6-fluoro-4-pyridyl)carbamate (200 mg) as a colorless oil. Platinumdioxide (10 mg) was added under nitrogen to a solution of benzyl N-(2-chloro-6-fluoro-4-pyridyl)carbamate in methanol (20 mL) and the mixture was stirred under hydrogen atmospohere for 16 hours at 25C. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by prep-HPLC (Column: Phenomenex Gemini 150*25mm* 10um. Condition: 0.05%ammonia-ACN). The obtained solid was dried resulting in 2-chloro-6-fluoro-pyridin-4-amine (33 mg) as a white solid. 1H NMR (400MHz, DMSO-d6) δ = 6.83 (br. s., 2H), 6.46 (t, J=1.6 Hz, 1H), 6.06 (d, J=1.6 Hz, 1H).
 

Historical Records

Technical Information

Categories