Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 439931-33-6 | MDL No. : | MFCD02931394 |
Formula : | C9H11ClN2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 198.65 | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine In dichloromethane at 0℃; for 2h; | 12 Example 12; Synthesis of 2-chloro-N-isopropyI-isonicotinamide; To a stirred suspension of 20.0O g 2-chloroisonicotinic acid (123.2 mmol) in 20O mL acetonitrile were added 11.77 mL thionyl chloride (160.2 mmol, 1.3 eq) and 762 μL DMF (9.86 mmol, 0.08 eq). The mixture was heated to reflux and was monitored by HPLC. After 60 min (< 1 % of 2-chloroisonicotinic acid), the reaction mixture was cooled to room temperature and all volatiles were removed in a rotary evaporator (40° C/10 mbar). The residual oil was dissolved in 200 mL dichloromethane and the solution was cooled to 0° C. 20.6 mL triethylamine (147.8 mmol, 1.20 eq) and 11.7 mL isopropylamine (135.5 mmol, 1.10 eq) were subsequently added and stirring was continued for 2 h at 0° C until the solution turned almost black. The mixture was poured on 200 mL water and phases were separated. The organic phase was washed with 20O mL brine, dried over 15 g sodium sulfate and filtered. The filter cake was washed with 3O mL dichloromethane. After removal of solvent in a rotary evaporator (40° C, 20 mbar), the crude product (24.83 g, 102 % w/w) was obtained as a brown solid (HPLC purity 98.6 % area). Mp: 99° C (decomp.) ;1H NMR (300 MHz, CDCl2): δ 8.50 (dd, IH, J = 4.9 Hz, J= 0.6 Hz), 7.62 (dd, IH, J =1.3 Hz, J= 0.6 Hz), 7.51 (dd, IH, J= 5.1 Hz, J= 1.5 Hz), 5.94 (br. s, IH), 4.27 (m, IH), 1.28 (d, 6H, J= 6.6 Hz) ppm ;13C NMR ClOO MHz, CDClO: δ 163.4, 152.4, 150.4, 145.1, 122.0, 119.8, 42.5, 22.6 ppm. |
With triethylamine In benzene for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-chloroisonicotinic acid, With thionyl chloride; N,N-dimethyl-formamide In acetonitrile for 1h; Heating; Stage #2: isopropylamine With triethylamine In dichloromethane at 0℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In methanol at 80℃; for 24h; | 13 Example 13:; Synthesis ofiV-isopropyl-2-methoxy-isonicotinamide; To a stirred solution of 19.44 g 2-chloro-iV-isopropyl-isonicotinamide (97.86 mmol) as obtainable from example 12, in 165 mL methanol were added 27.82 g NaOMe (489.3 mmol, 5.0 eq) in four equal portions over 60 min. The solution was then heated to 80° C and the reaction was monitored by HPLC. After 23 h (< 2 % area starting material 2-chloro-iV-isopropyl-isonicotinamide), the mixture was cooled to room temperature and EPO quenched by addition of 200 mL saturated aqueous NH4Cl. The product was extracted three times with 150 mL, in total 450 mL dichloromethane. The combined organic phases were dried over 40 g Na2SO4 (30 min) and filtered. The filter cake was washed with 80 mL dichloromethane. After removal of solvent in a rotary evaporator (40° C, 22 mbar), the crude product (15.856 g, 83 % w/w, HPLC purity 93.7 % area) was obtained as a white solid. Mp: 100° C.1H NMR GOO MHz, CDCh): δ 8.24 (dd, IH, J = 5.3 Hz, J = 0.6 Hz), 7.15 (dd, IH, J = 5.3 Hz, J= 1.3 Hz), 7.02 (dd, IH, J= 1.3 Hz, J= 0.6 Hz), 5.89 (br. s, IH), 4.28 (m, IH), 3.96 (s, 3H), 1.26 (d, 6H, J= 6.6 Hz) ppm ;13C NMR ClOO MHz, CDClO: δ 165.34, 165.26, 148.3, 145.6, 114.5, 109.1, 54.3, 42.7, 23.2 ppm. |
In methanol at 80℃; for 23h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: methanol / 23 h / 80 °C 2.1: TMEDA; n-BuLi / various solvent(s); hexane / 6 h / -78 - -22 °C 2.2: various solvent(s); hexane / 16.75 h / -78 °C 3.1: propan-2-ol; H2O / 3 h / 20 °C 3.2: 5.486 g / aq. HCl / propan-2-ol / 20 - 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: methanol / 23 h / 80 °C 2.1: TMEDA; n-BuLi / various solvent(s); hexane / 6 h / -78 - -22 °C 2.2: various solvent(s); hexane / 16.75 h / -78 °C 3.1: propan-2-ol; H2O / 3 h / 20 °C 3.2: 5.486 g / aq. HCl / propan-2-ol / 20 - 50 °C 4.1: Et3Al / cyclohexane; benzene; toluene / 0.25 h / 0 °C 4.2: 53 percent / cyclohexane; toluene; tetrahydrofuran / 3 h / -40 - -15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: methanol / 23 h / 80 °C 2.1: TMEDA; n-BuLi / various solvent(s); hexane / 6 h / -78 - -22 °C 2.2: various solvent(s); hexane / 16.75 h / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: methanol / 23 h / 80 °C 2.1: TMEDA; n-BuLi / various solvent(s); hexane / 6 h / -78 - -22 °C 2.2: various solvent(s); hexane / 16.75 h / -78 °C 3.1: propan-2-ol; H2O / 3 h / 20 °C 3.2: 5.486 g / aq. HCl / propan-2-ol / 20 - 50 °C 4.1: Et3Al / cyclohexane; benzene; toluene / 0.25 h / 0 °C 4.2: 53 percent / cyclohexane; toluene; tetrahydrofuran / 3 h / -40 - -15 °C 5.1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: methanol / 23 h / 80 °C 2.1: TMEDA; n-BuLi / various solvent(s); hexane / 6 h / -78 - -22 °C 2.2: various solvent(s); hexane / 16.75 h / -78 °C 3.1: propan-2-ol; H2O / 3 h / 20 °C 3.2: 5.486 g / aq. HCl / propan-2-ol / 20 - 50 °C 4.1: Et3Al / cyclohexane; benzene; toluene / 0.25 h / 0 °C 4.2: 53 percent / cyclohexane; toluene; tetrahydrofuran / 3 h / -40 - -15 °C 5.1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C 6.1: LHMDS / tetrahydrofuran / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: methanol / 23 h / 80 °C 2.1: TMEDA; n-BuLi / various solvent(s); hexane / 6 h / -78 - -22 °C 2.2: various solvent(s); hexane / 16.75 h / -78 °C 3.1: propan-2-ol; H2O / 3 h / 20 °C 3.2: 5.486 g / aq. HCl / propan-2-ol / 20 - 50 °C 4.1: Et3Al / cyclohexane; benzene; toluene / 0.25 h / 0 °C 4.2: 53 percent / cyclohexane; toluene; tetrahydrofuran / 3 h / -40 - -15 °C 5.1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C 6.1: LHMDS / tetrahydrofuran / -95 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: methanol / 23 h / 80 °C 2.1: TMEDA; n-BuLi / various solvent(s); hexane / 6 h / -78 - -22 °C 2.2: various solvent(s); hexane / 16.75 h / -78 °C 3.1: propan-2-ol; H2O / 3 h / 20 °C 3.2: 5.486 g / aq. HCl / propan-2-ol / 20 - 50 °C 4.1: Et3Al / cyclohexane; benzene; toluene / 0.25 h / 0 °C 4.2: 53 percent / cyclohexane; toluene; tetrahydrofuran / 3 h / -40 - -15 °C 5.1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C 6.1: LHMDS / tetrahydrofuran / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: methanol / 23 h / 80 °C 2.1: TMEDA; n-BuLi / various solvent(s); hexane / 6 h / -78 - -22 °C 2.2: various solvent(s); hexane / 16.75 h / -78 °C 3.1: propan-2-ol; H2O / 3 h / 20 °C 3.2: 5.486 g / aq. HCl / propan-2-ol / 20 - 50 °C 4.1: Et3Al / cyclohexane; benzene; toluene / 0.25 h / 0 °C 4.2: 53 percent / cyclohexane; toluene; tetrahydrofuran / 3 h / -40 - -15 °C 5.1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C 6.1: LHMDS / tetrahydrofuran / 2 h / -78 °C 6.2: tetrahydrofuran / 1.5 h / -95 - -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: methanol / 23 h / 80 °C 2.1: TMEDA; n-BuLi / various solvent(s); hexane / 6 h / -78 - -22 °C 2.2: various solvent(s); hexane / 16.75 h / -78 °C 3.1: propan-2-ol; H2O / 3 h / 20 °C 3.2: 5.486 g / aq. HCl / propan-2-ol / 20 - 50 °C 4.1: Et3Al / cyclohexane; benzene; toluene / 0.25 h / 0 °C 4.2: 53 percent / cyclohexane; toluene; tetrahydrofuran / 3 h / -40 - -15 °C 5.1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C 6.1: LHMDS / tetrahydrofuran / 2 h / -78 °C 6.2: tetrahydrofuran / 1.5 h / -95 - -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: methanol / 23 h / 80 °C 2.1: TMEDA; n-BuLi / various solvent(s); hexane / 6 h / -78 - -22 °C 2.2: various solvent(s); hexane / 16.75 h / -78 °C 3.1: propan-2-ol; H2O / 3 h / 20 °C 3.2: 5.486 g / aq. HCl / propan-2-ol / 20 - 50 °C 4.1: Et3Al / cyclohexane; benzene; toluene / 0.25 h / 0 °C 4.2: 53 percent / cyclohexane; toluene; tetrahydrofuran / 3 h / -40 - -15 °C 5.1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C 6.1: LHMDS / tetrahydrofuran / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: methanol / 23 h / 80 °C 2.1: TMEDA; n-BuLi / various solvent(s); hexane / 6 h / -78 - -22 °C 2.2: various solvent(s); hexane / 16.75 h / -78 °C 3.1: propan-2-ol; H2O / 3 h / 20 °C 3.2: 5.486 g / aq. HCl / propan-2-ol / 20 - 50 °C 4.1: Et3Al / cyclohexane; benzene; toluene / 0.25 h / 0 °C 4.2: 53 percent / cyclohexane; toluene; tetrahydrofuran / 3 h / -40 - -15 °C 5.1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C 6.1: LHMDS / tetrahydrofuran / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: methanol / 23 h / 80 °C 2.1: TMEDA; n-BuLi / various solvent(s); hexane / 6 h / -78 - -22 °C 2.2: various solvent(s); hexane / 16.75 h / -78 °C 3.1: propan-2-ol; H2O / 3 h / 20 °C 3.2: 5.486 g / aq. HCl / propan-2-ol / 20 - 50 °C 4.1: Et3Al / cyclohexane; benzene; toluene / 0.25 h / 0 °C 4.2: 53 percent / cyclohexane; toluene; tetrahydrofuran / 3 h / -40 - -15 °C 5.1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C 6.1: LHMDS / tetrahydrofuran / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / 1 h / Heating 2: triethylamine / benzene / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-chloro-N-isopropylisonicotinamide With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Stage #2: With water-d2 In tetrahydrofuran at -78℃; for 0.5h; |