Methyl 4,6-dichloronicotinate
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Methyl 4,6-dichloronicotinate
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CAS No:
65973-52-6
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Formula:
C7H5Cl2NO2
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Chemical Name:
Methyl 4,6-dichloronicotinate
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Synonyms:
4,6-Dichloronicotinic acid methyl ester;Methyl 4,6-dichloronicotinate;methyl 4,6-dichloropyridine-3-carboxylate;Methyl 4,6-dichloronicotinate 95+%;3-Pyridinecarboxylic acid, 4,6-dichloro-, Methyl ester;Methyl 4,6-dichloropyridine-3-carboxylate, 2,4-Dichloro-5-(methoxycarbonyl)pyridine;Methyl 4,6-dichloronicotinte;4,6-Dichloro-pyridin-3-carboxylic acid methyl ester
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CAS No:
Safety Information
IRRITANT
22
24/25
Xn
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 4 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Methyl 4,6-dichloronicotinate Use and Manufacturing
4, 6-Dihydroxy-nicotinic acid methyl ester (3.9 g, 23 mmol) (from Example 7 supra) was added to POCl4, 6-Dihydroxy-nicotinic acid methyl ester (25.7 g, 152 mmol) was dissolved in POCl[00215] Step A: Methyl 4.6-dichloronicotinate: After B (199.0 g, 1.18 mol) was dissolved in N, N-dimethylaniline (285.4 g, 2.36 mol)Was added to 1.6 L of phosphorus oxychloride (POCl3) and the mixture was refluxed.After 4 h the reaction mixture was concentrated, the residue was poured into water, use Ethyl acetate (1.0 L x 3). The organic layer was dried and concentrated to 500 mL using a silica gel column (mobile phase petroleum) Ether: ethyl acetate = 60: 1) to give 168.7 g of product C in 70percent yield.To a solution of methyl 4, 6-dihydroxynicotinate (900 g, 5.3 mol) in phosphoryl chloride (4000 mL) was added NN-diethyl aniline (1035 mL, 6.4 mol). The reaction was heated to 120 °C for 2 h and then allowed to cool to room temperature. The reaction mixture was reduced in vacuo and poured slowly onto ice portionwise. The mixture was extracted with EtOAc (2x). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product was purified via flash chromatography on silica gel (solvent gradient: 0percent-5percent EtOAc in petroleum ether) to afford methyl 4, 6-dichloronicotinate (400 g, yield 42 percent). LCMS (ESI) [M+H] = 206.1 ; 'H NMR (400 MHz, DMSO- dA mixture of 4, 6-dihydroxy-nicotinic acid methyl ester (9.10 g, 53.8 mmol) in POClPREPARATION. 84 4, 6-Dichloro-nicotinic acid methyl ester 3-Pyridinecarboxylic acid [(27g, 160mmol), J.Het. Chem, 20, 1363; 1983] was added portionwise to phosphorus oxychloride (180mL) and the mixture was . heated under reflux for 7 hours and-stirred at room temperature for 18-HOURS. The mixture was then-concentrated in-vacuo to a low volume and. the residue was quenched with water The aqueous mixture was NEUTRALISED WITH SODIUM hydrogen carbonate solution and extracted with chloroform (3x150mL). The combined organic solutions were washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound as a red oil in 83percent yield, 27.2g, 1HNMR (CDCL3, 400MHZ) No.: 3.96(S, 3H), 7.47(S, 1H), 8.85(S, 1H), MS APCI+ M/Z 206 [MH]+
Computed Properties
Molecular Weight:206.02
XLogP3:2.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:204.9697338
Monoisotopic Mass:204.9697338
Topological Polar Surface Area:39.2
Heavy Atom Count:12
Complexity:177
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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