5-CHLORO-3-METHYL-PYRIDINE-2-CARBOXYLIC ACID synthesis
- Product Name:5-CHLORO-3-METHYL-PYRIDINE-2-CARBOXYLIC ACID
- CAS Number:886365-46-4
- Molecular formula:C7H6ClNO2
- Molecular Weight:171.58
156072-84-3
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Yield:886365-46-4 89%
Reaction Conditions:
in ethanol
Steps:
240.2 Step 2:
Step 2:
Synthesis of 5-chloro-3-methylpicolinic acid
To a solution of 5-chloro-3-methylpicolinonitrile (24.0 g, 157 mmol) in EtOH (100 mL) was added NaOH 5.0N (110 ml, 550 mmol).
The resulting mixture was refluxed at 90° C. for 18 h.
After cooling to RT, the reaction mixture was concentrated, diluted with water and the pH of the solution was adjusted to 4 by addition of 5N HCl.
The solid that precipitated was filtered and set aside.
The filtrate was extracted with EtOAc (2*).
The aqueous layer was again acidified with 5N HCl to pH 4 and extracted with EtOAc (2*).
The EtOAc extracts were combined, dried, and concentrated.
The solid obtained from all the workup steps were combined and dried in a high vac oven at 40° C. for 12 h to give the title compound 5-chloro-3-methylpicolinic acid (24.1 g, 140 mmol, 89% yield). LC/MS (ESI+) m/z=172.0 (M+H); 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 11.29 (br. s., 1H), 8.41 (d, J=1.76 Hz, 1H), 7.73 (d, J=1.76 Hz, 1H), 2.75 (s, 3H).
References:
MINATTI, Ana Elena;LOW, Jonathan D.;ALLEN, Jennifer R.;CHEN, Jian;CHEN, Ning;CHENG, Yuan;JUDD, Ted;LIU, Qingyian;LOPEZ, Patricia;QIAN, Wenyuan;RUMFELT, Shannon;RZASA, Robert M.;TAMAYO, Nuria A.;XUE, Qiufen;YANG, Bryant;ZHONG, Wenge US2014/249104, 2014, A1 Location in patent:Page/Page column
16110-09-1
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65550-77-8
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886365-46-4
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