| Identification | Back Directory | [Name]
6-Chloro-4-methoxynicotinic acid | [CAS]
716362-10-6 | [Synonyms]
6-Chloro-4-methoxynicotinicAci
6-Chloro-4-methoxynicotinic acid
6-chloro-4-Methoxypyridine-3-carboxylic acid
6-Chloro-4-methoxy-3-pyridinecarboxylic acid
3-Pyridinecarboxylic acid, 6-chloro-4-Methoxy- | [Molecular Formula]
C7H6ClNO3 | [MDL Number]
MFCD10000638 | [MOL File]
716362-10-6.mol | [Molecular Weight]
187.58 |
| Chemical Properties | Back Directory | [Boiling point ]
350.7±37.0 °C(Predicted) | [density ]
1.430 | [storage temp. ]
Inert atmosphere,2-8°C | [pka]
3.13±0.10(Predicted) | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C7H6ClNO3/c1-12-5-2-6(8)9-3-4(5)7(10)11/h2-3H,1H3,(H,10,11) | [InChIKey]
DFXUFJAAXAJWSA-UHFFFAOYSA-N | [SMILES]
C1=NC(Cl)=CC(OC)=C1C(O)=O |
| Hazard Information | Back Directory | [Uses]
6-Chloro-4-methoxynicotinic acid is used for preparation of benzimidazolylazabicyclooctylethylpiperidines as Ccr5 antagonists for the treatment of HIV infection.
| [Synthesis]
General procedure for the synthesis of 6-chloro-4-methoxynicotinic acid from methyl 6-chloro-4-methoxynicotinate: lithium hydroxide (1.84 g, 43.9 mmol) was added to a solution of the intermediate from step 2 (2.94 g, 14.6 mmol) in a mixture of methanol (30 mL), tetrahydrofuran (30 mL) and water (3 mL) at 0°C. The reaction mixture was stirred at room temperature for 3 hours. The volatiles were removed under reduced pressure and the residue was diluted with water and washed with dichloromethane. The aqueous layer was acidified to pH ≈ 3 with sodium bisulfate solution and extracted with dichloromethane. The combined organic layers were dried and the volatiles were removed under reduced pressure to give the target product 6-chloro-4-methoxynicotinic acid (2.7 g, 98% yield). | [References]
[1] Patent: US2015/166505, 2015, A1. Location in patent: Paragraph 0342; 0349; 0350
[2] Patent: WO2012/110860, 2012, A1. Location in patent: Page/Page column 99 |
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