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CAS No. :5221-37-4 MDL No. :MFCD00023426
Formula : C7H7ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :JJMRJPAPJCFDAM-UHFFFAOYSA-N
M.W : 170.60 Pubchem ID :289435
Synonyms :

Safety of [ 5221-37-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 5221-37-4 ]

* 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.

  • Upstream synthesis route of [ 5221-37-4 ]
  • Downstream synthetic route of [ 5221-37-4 ]

[ 5221-37-4 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 504-29-0 ]
  • [ 79-04-9 ]
  • [ 5221-37-4 ]
YieldReaction ConditionsOperation in experiment
97%
Stage #1: at 80℃; for 0.0833333 h; Microwave irradiation
Stage #2: With sodium hydroxide In water; 1,2-dichloro-ethane
2-aminopyridine (2.8 g, 30 mmol) was dissolved in dichloroethane (25 ml) in a 50 ml-glass vessel and chloroacetyl chloride was added dropwise thereto. The glass vessel was capped with a TFM teflon cover and placed in a rotor in a microwave reactor. The mixture was irradiated by microwave at 300 W and 80° C., for 5 min. After irradiating for 5 min., the reaction mixture was adjusted to pH9 with a saturated aqueous solution of sodium hydroxide and extracted twice with dichloroethane. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed by using a rotary evaporator and the desired pink solid product of 4.9 g (97percent) was obtained by recrystallization with acetonitrile. mp 110-115° C.; IR (KBr) 3443, 3226, 1683, 1581, 1330, 1198, 775 cm-1; 1H NMR (CDCl3) 4.2 (2H, s), 7.1 (1H, d), 7.7 (1H, t), 8.2 (1H, d, J=8.3 Hz), 8.4 (1H, d, J=4.9 Hz), 8.95 (1H, bs); 13C NMR (CDCl3) 43.2, 111.4, 121.0, 139.1, 148.2, 150.7, 164.9; EIMS m/z 170.6 (M+)
89.3% With triethylamine In dichloromethane at 0 - 25℃; General procedure: 2-Chloroacetyl chloride (24 mmol) was slowly added dropwise to a mixture of R-NH2 (20 mmol) and Et3N (24 mmol, 3.3 mL) in anhydrous CH2Cl2 (20 mL) at 0 °C. The reaction mixture was warmed to room temperature and stirred for an additional 20 h. After the solvent was removed under reduced pressure, the residue was washed with ice water (3 .x. 20 mL) and the precipitate was separated by filtration. The crude product was purified by crystallization from a mixture solvent of Et2O/petroleum.
79% With triethylamine In dichloromethane at 0 - 20℃; for 3 h; Inert atmosphere Example 1
Preparation of N-2-(2-Chloroethyl)amidopyridine (1)
Chloroacetyl chloride (2.39 mL, 32.97 mmol) was slowly added to the mixture of 2-aminopyridine (1.88 g, 19.98 mmol) and TEA (4.30 mL, 30.69 mmol) in dry dichlorometane (100 mL) at 0° C.
The reaction mixture was stirred at room temperature under an Ar atmosphere for 3 h.
The organic layer was extracted with CH2Cl2, washed with water, and dried over anhydrous MgSO4.
The residue was purified by flash column chromatography (3:1 hexane/ethyl acetate) to give product (2.68 g, 79percent) as a white solid.
1H NMR (CDCl3, 300 MHz) δ 4.20 (s, 2H), 7.09-7.14 (m, 1H), 7.77 (m, 1H), 8.22-8.28 (m, 2H), 9.45 (s, 1H); 13C NMR (CDCl3, 75 MHz) δ 42.8, 114.3, 120.5, 139.1, 147.1, 150.4, 164.7; HRMS (FAB+, m-nitrobenzylalcohol): Calcd for C7H8ON2Cl: 171.0325, Found: 171.0324.
78.7% With pyridine In chloroform at 0 - 20℃; for 4.25 h; 2-Chloroacetyl chloride (0.39 mL, 5.0 mmol) was dissolved in chloroform (20 mL), then added dropwise to a cooled, stirred solution of 2-aminopyridine (380.2 mg, 4.0 mmol) and pyridine (0.41 mL, 5.0 mmol) in chloroform (20 mL) within 15 min. After stirred for 4 h at room temperature, the liquid was removed under reduced pressure to obtain a pale red-brown solid. It was purified by silica gel column chromatography using DCM/methanol (20:1, v/v) as eluent to afford 537.4 mg (78.7percent yield) of product. IR (KBr): 3385 (N-H), 3362 (N-H), 1689 (CO). 1H NMR (DMSO-d6, 300 MHz) δ 10.80 (s, 1H), 8.34 (d, 1H), 8.04 (d, 1H), 7.82 (t, 1H), 7.14 (t, 1H), 4.35 (s, 2H). 13C NMR (DMSO-d6, 300 MHz): δ 166.5, 151.3, 147.1, 140.5, 120.7, 114.7, 44.0. Anal. Calcd for C7H7ClN2O (170.60): C, 49.28; H, 4.14; N, 16.42percent. Found: C, 49.27; H, 4.15; N, 16.42percent.
78.5% With triethylamine In dichloromethane at 20℃; for 3 h; A solution of 2-aminopyridine (188mg, 2mmol) and 0.3mL trimethylaminein was stirred for 30min at°C in CH2Cl2. Then chloroacetyl chloride (0.175mL, 2.2mmol) was added to the solution, and the mixture was stirred for 3h at room temperature. After the reaction, the solution was extracted with H2O (5mL×3), then the combined organic layer was concentrated under reduced pressure. The crude product was purified by column chromatography with CH2Cl2/EtOAC (v/v, 3:1) to get the target compound 5 (270mg, 78.5percent). 1H NMR (500MHz, CDCl3): δ 8.87 (s, 1H), 8.33-8.32 (d, 1H, J=5), 8.21-8.18 (d, 1H, J=15), 7.77-7.72 (m, 1H), 7.09-7.13 (m, 1H), 4.21 (s, 2H).
78% With triethylamine In dichloromethane at 20℃; for 5 h; General procedure: Substituted aminopyridine (2a-e, 20 mmol) was added to a 100 mL reaction flask, 20 mL of dry methylene chloride was used as solvent,After addition of chloroacetyl chloride (24 mmol) was completely dissolved, triethylamine (24 mmol) was slowly added dropwise to the reaction flask, TLC (CH2Cl2:CH3OH = 30: 1). The reaction was quenched by stirring at room temperature for 5 h. After completion of the reaction, the dichloromethane was distilled off under reduced pressureWater and ethyl acetate. The organic phase was dried over anhydrous Na2SO4 and the residue was purified by flash column chromatography to giveUnder the target object 3a-e.3a: white solid; yield 78percent
78.5%
Stage #1: With triethylamine In dichloromethane at 0℃; for 0.5 h;
Stage #2: at 20℃; for 3 h; Inert atmosphere
A 50 mL round bottom flask was taken, and 2 mmol (188 mg) of 2-aminopyridine was added at 0 ° C, followed by anhydrous dichloromethane (15 mL) mixed with triethylamine (0.3 mL).Stir well for 30 minutes.Then, under ice-cooling conditions, 2.2 mmol (0.175 mL, mixed 5 mL of dichloromethane) of chloroacetyl chloride was added dropwise to the above mixture, and the reaction mixture was reacted under nitrogen atmosphere at room temperature for 3 hours after the dropwise addition.After confirming the completion of the reaction, the reaction mixture was washed twice with 30 mL of saturated saline, washed with 20 mL of water, and extracted, and this was repeated three times.The organic phase was dried over anhydrous sodium sulfate and filtered and evaporated to dryness.Ethyl acetate = 3:1 (v: v) was used as an eluent to afford 0.27 g of yello. The yield was 78.5percent.
64% With triethylamine In dichloromethane at 0 - 20℃; for 18 h; Inert atmosphere To a solution of 2-aminopyridine (2 g, 21.3 mmol) and TEA (3.23 g, 31.9 mmol, 4.4 mL) in anhydrous DCM (20 mL) was slowly added chloroacetyl chloride (3.96 g, 35.1 mmol, 2.8 mL) at 0°C. The reaction mixture was stirred at room temperature under a nitrogen atmosphere for 18 h. The reaction mixture was partitioned between DCM (50 mL) and water (50 mL); the organic portion was dried (phase separation cartridge) and evaporated to dryness to afford a brown oil.The residue was purified by column chromatography on silica gel eluting with petroleum ether (A): ethyl acetate (B) (15-50percent (B), 40 g, 10.0 CV, 40 mL/min) to afford a beige solid (2.31 g, 64percent). The 1H NMR indicated presence of both starting materials so the product was re-purified by column chromatography on highperformance silica gel eluting with petroleum ether (A): ethyl acetate (B) (40-75percent (B), 40 g, 18.3 CV, 40 mL/min) to afford the product as a beige solid (1 .92 g, 53percent).LC-MS: m/z calcd for C7H7C1N20, 170.0; found, 171.0 (M+H)+.? NMR (300 MHz, CDCI3): ?? 4.18 (2H, s, CH2), 7.06-7.10 (1H, m, pyridyl-5-CH), 7.68-7.75 (1H, m, pyridyl-4-CH), 8.17 (1H, d, J = 8.3 Hz, pyridyl-3-CH), 8.30 (1H, dd, J = 4.9 Hz and 1.0 Hz, pyridyl-6-CH) and 8.98 (1 H, s, NH). 13C NMR (75 MHz, CDCI3): 5C 42.8 (CH2), 1 13.9 (pyridyl-3-CH), 120.5 (pyridyl-5-CH), 138.5 (pyridyl-4- CH), 147.9 (pyridyl-6-CH), 150.4 (pyridyl-2-CN) and 164.5 (C=0).
62% at 60℃; for 0.5 h; To a solution of 1 (941 mg, 10 mmol) in dry DMF (5 mL) at room temperature was added dropwise chloroacetyl chloride (1.69 g, 15 mmol). A solid mixture quickly formed after addition of the acid chloride, which was then heated at 60° C. for 30 min. The mixture was cooled down to room temperature, diluted with Et2O, and the solid was filtered. The solid was treated with satd. NaHCO3, washed with H2O, and air-dried to give 2-chloro-N-pyridin-2-yl-acetamide as a solid (1.05 g, 62percent). MS: m/z 171.16 (M+H)+. To a solution of the crude 2-chloro-N-pyridin-2-yl-acetamide (171 mg, 1 mmol) in DMA (2 mL) was added 1-Boc-piperazine (373 mg, 2 mmol) and the solution was heated at 90° C. for 2 h. The mixture was cooled to room temperature, diluted with H2O, treated with satd. NaHCO3 and extracted with EtOAc. The organic extract was dried over MgSO4, and concentrated in vacuo to give 4-(Pyridin-2-ylcarbamoylmethyl)-piperazine-1-carboxylic acid tert-butyl ester (154 mg, 48percent), which was treated with 4M HCl in dioxane (5 mL) at room temperature for 16 h. The solvent was removed and the residue vacuum-dried to give 2 as a light pink solid. MS: m/z 221.26 (M+H)+.
53% With triethylamine In dichloromethane at 0 - 20℃; for 18 h; Inert atmosphere To a solution of 2-aminopyridine (2 g, 21.3 mmol) and TEA (3.23 g, 31.9 mmol, 4.4 ml .) in anhydrous DCM (20 mL) was slowly added chloroacetyl chloride (3.96 g, 35.1 mmol, 2.8 mL) at 0°C. The reaction mixture was stirred at room temperature under a nitrogen atmosphere for 18 h. The reaction mixture was partitioned between DCM (50 mL) and water (50 mL); the organic portion was dried (phase separation cartridge) and evaporated to dryness to afford a brown oil .The residue was purified by column chromatography on silica gel eluting with petroleum ether (A): ethyl acetate (B) (15-50percent (B), 40 g, 10.0 CV, 40 mL min) to afford a beige solid (2.31 g. 64percent). The 1 H NMR indicated presence of both starting materials so the product was re-purified by column chromatography on hi h performance silica gel eluting with petroleum ether (A): ethyl acetate (B) (40-75percent (B), 40 g, 18.3 CV, 40 mL/min) to afford the product as a beige solid (1.92 g, 53percent).LC-MS: m/z calcd for C7H7C1N20, 170.0; found. 171.0 (M+H)+..H NMR (300 MHz, CDCk): δΗ 4.18 (2H, s, Cil2). 7.06-7.10 (1H, m, pyridyl-5-CH), 7.68-7.75 (1H, m. pyridyl-4-CH), 8. 1 7 (1H, d, J = 8.3 Hz, pyridyi-3-CH), 8.30 ( Hi, del, J = 4.9 Hz and 1.0 Hz, pyridyl-6-CH) and 8.98 ( 1 11, s, NH). 13C NMR (75 MHz, CDC13): δ,:· 42.8 (CH2), 1 13.9 (pyridyl-3-CH), 120.5 (pyridyl-5-CH). 138.5 (pyridyi-4- CH), 147.9 (pyridyl-6-CH), 1 50.4 (pyridyl-2-CN) and 164.5 (C=0).
39% at 20℃; General procedure: A solution of Aryl-or heteroary-amine (1.0 mol) in chloroformor dichloromethane was stirred with potassium carbonate(1.5 mol). To this solution was then added 1.5 mol of chloroacetylchloride under cold. Reaction was stirred overnight at room temperature.After completion of reaction (monitored by TLC), solventwas removed under reduced pressure. To the solid mass, ice coldwater was added. The solid thus obtained was then filtered driedand recrystallized from ethanol.
33% With triethylamine In chloroform at 0 - 5℃; for 12 h; Inert atmosphere General procedure: To a solution of theappropriate amine (31-44, 10 mmol) and triethylamine (10 mmol) in anhydrous chloroform was added dropwisechloroacetylcloride (30, 12 mmol) at0-5 °C and the mixture was stirred for 12 h at the same temperature under N2.Then the solvent was removed under vacuum, and the residue dissolved in ethylacetate was once washed with water. The organic phase was stirred with 10percentactivated charcoal for 30 min and filtered through a neutral alumina bed.Finally, the solvent was distilled under vacuum. It is worth mentioning thatall the products obtained decompose rapidly, therefore they were used immediatelyin the next reaction. a) 2-Chloro-N-(pyridin-2-yl)acetamide(16) Obtained as a lightgrey solid (33percentyield); mp 104 °C. 1H NMR (DMSO-d6;300 MHz): δ 12.90 (s, 1H), 8.35 (ddd, J= 4.9, 1.9, 0.8 Hz, 1H), 8.20 (d, J =8.3 Hz, 1H), 7.84 (dd, J = 7.6, 2.1Hz, 1H), 7.16 (ddd, J = 7.4, 4.9, 1.0Hz, 1H), 2.71 (s, 2H). 13C NMR (DMSO-d6; 75 MHz): δ 164.62, 150.56, 148.14, 138.63, 120.62,114.09, 42.91. GC-MS m/z (percent): 170 (M+, 20); 135 (M-35+, 100); 121 (M-49+, 15);94 (M-76+, 95).
68% With sodium hydrogencarbonate; triethylamine In dichloromethane PREPARATION EXAMPLE 4
Preparation of Compound 4
2-Aminopyridine (2 g, 21.3 mmol), chloroacetyl chloride (2.5 mL, 31.4 mmol) and Et3N (4.4 mL, 31.8 mmol) were dissolved in dichloromethane (CH2Cl2, 100 mL).
The reaction mixture was stirred at room temperature for 17 hours, after which the organic phase was washed with an aqueous solution of NaHCO3 (10percent, w/v).
The organic layer was dried with anhydrous MgSO4 and then filtered.
The filtrate was evaporated to dryness.
The residue was purified using flash chromatography (CH2Cl2), yielding 2.46 g (68percent) of 2-(chloroacetyl)amidopyridine.

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  • [ 79-11-8 ]
  • [ 5221-37-4 ]
YieldReaction ConditionsOperation in experiment
80% With dicyclohexyl-carbodiimide In dichloromethane at 40℃; for 2 h; Inert atmosphere 2-Aminopyridine (0.47 g, 5 mmol) was added to a solution of chloroacetic acid (5 mmol) in 10 mL of CH2Cl2. The resulting mixture was treated with DCC (1.03 g, 5 mmol) in 10mL of CH2Cl2 with stirring under N2. This mixture was kept at 40 C for 2h and then at room temperature for 15 min, filtered, and the precipitate was washed with dry diethyl ether. The pale brown filtrate was evaporated, and the yellow-brown solid so obtained was purified by chromatography on SiO2, eluting with diethylether/ethyl acetate, to yield 680 mg (80percent) of white crystals which turned red-purple on exposure to air
Reference: [1] Australian Journal of Chemistry, 2015, vol. 68, # 4, p. 687 - 692
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  • [ 5221-37-4 ]
Reference: [1] Australian Journal of Chemistry, 2015, vol. 68, # 4, p. 687 - 692
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