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CAS No. : | 630082-81-4 | MDL No. : | MFCD06255138 |
Formula : | C8H8ClNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 185.61 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
88% | To a solution of 6-chloro-2,4-dimethyl-nicotinic acid ethyl ester (0.200 g, 0.930 mmol) in EtOH (1 mL) was added 4N NaOH (1 mL), and the mixture was heated at 90 C. for 1 h. After the mixture was cooled to room temperature EtOH was removed and the aqueous residue was acidified with 4N HCl to afford a white precipitate. The precipitate (0.152 g, 88%) was collected by filtration and dried under vacuum to give 6-chloro-2,4-dimethyl-nicotinic acid as a white solid. 1H NMR (CD3OD) δ 2.37 (s, 3H), 2.51 (s, 3H), 7.23 (s, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 26% 2: 52% | Stage #1: 6-chloro-2,4-dimethylnicotinonitrile With sulfuric acid In water at 120℃; for 16h; Stage #2: With sodium nitrite In water at 90℃; for 3h; | 69.1; 60.1 Step 1: 6-Chloro-2,4-dimethylnicotinic acid 6-Chloro-2,4-dimethylnicotinonitrile (5.0 g, 30.01 mmol, 1 eq) was dissolved in a mixture of sulfuric acid (10.4 mL, 195.07 mmol, 6.5 eq) and water (9 mL). The mixture was heated at 120 °C for 16 hrs. Then it was then cooled to 90 °C and sodium nitrite (14.49 g, 210.07 mmol, 7 eq) was added in small portions over 10 minutes. The reaction was heated at 90 °C for an additional hour. Then other 3.5 eq. of NaNC were added portionwise and the mixture was stirred at 90 °C for additional 2 hrs. The mixture was cooled to r.t. and poured into an ice-water mix. The chilled mixture was basified to pH = 12 using NaOH aq. 10N. The aqueous mixture was then washed with DCM (2x) to remove impurities. The pH was then adjusted to 2 by adding HC1 aq. 6N and a mixture 4: 1 of DCM/MeOH was added. The off- white solid at the interphase was recovered by filtration and proved to be 6-hydroxy-2,4- dimethylpyridine-3 -carboxylic acid (1.3 g, 7.77 mmol, 26% yield). NMR (400 MHz, DMSO-de) d 12.90 - 11.00 (m, 2H), 6.05 (s, 1H), 2.30 (s, 3H), 2.18 (s, 3H). MS-ESI (m/z) calculated for CsHioNCb [M+H]+: 168.1. Found 168.2. The filtrate was also recovered, the 2 phases separated, the aqueous layer extracted with DCM/MeOH 4/1 (2x) and the combined extracts were washed with water, dried over anhydrous Na2S04 and concentrated to dryness to afford the title compound (2.9 g, 15.62 mmol, 52% yield). 'H NMR (400 MHz, DMSO-de) d 13.84 - 13.55 (bs, 1H), 7.34 (s, 1H), 2.45 (s, 3H), 2.31 (s, 3H). MS-ESI (m/z) calculated for C8H9CINO2 [M+H]+: 186.0. Found 186.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | Stage #1: 6-chloro-2,4-dimethylnicotinonitrile With sulfuric acid In water at 120℃; for 16h; Stage #2: With sodium nitrite In water at 90℃; for 18h; | 147.1 6-Chloro-2,4-dimethylnicotinonitrile (10.0 g, 60.02 mmol) was dissolved in a mixture of sulfuric acid (21.01 mL, 394.1 mmol) and water (20 mL). The mix ture was heated at 120 °C for 16 hrs. it was then cooled to 90 °C and sodium nitrite (29.41 g, 420.14 mmol) was added in small portions over 10 mm. The reaction was heated at 90 °C for an additional 18 hrs and then cooled to room temperature and poured into an ice-water mixture (-20 mL). The chilled mixture was filtered and the white solid wars washed with water. The white powder was dried under high vacuum to give the title compound (8.4 g, 45.26 mmol, 75% yield). 'H NMR (400 MHz, DMSO-r e) d ppm 13.51 (br. s., 1 H) 7.34 (s, 1 H) 2.45 (s, 3 H) 2.31 (s, 3 H). MS-ESI (m/z) calc’d for CsHsCINCh [M+H]+: 186.0. Found 186.0, 188.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | A suspension of 6-chloro-2,4-dimethylnicotinic acid (8.4 g, 45.26 mmol) in phosphorus(V) oxychloride (77.41 mL, 830.54 mmol) was heated at 80 C for 6 hrs. Excess POCb was removed by evaporation and the residue was carefully quenched with EtOH (112 mL) at 0 C. The solvent was evaporated and the residue was taken up in sat. aq. NaHCCb and stirred for 15 minutes. The solid that formed was extracted with DCM (3x) and the combined organic layers were passed through a phase separator and evaporated to dryness under reduced pressure. The crude material was purified by normal phase chromatography on a 100 g silica gel column, using a gradient of EtOAc in cyclohexane (from 0 to 20%) as eluent to afford the title compound (3.4 g, 15.91 mmol, 99% yield) a colorless oil. NMR (400 MHz, CDCb) d ppm 7.07 (s, 1H), 4.44 (q, J=7.0 Hz, 2H), 2.55 (s, 3H), 2.35 (s, 3H), (1717) 1.42 (t, J=7.2 Hz, 3H). MS-ESI (m/z) calc’d for C10H13CINO2 [M+H]+: 214.1. Found 214.0, 216.0 |