Ethyl 4,6-dichloropyridine-3-carboxylate → HCID 58962865, compound

HRID 917787Notes

Reaction equation

HRID 917787 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([Cl:13])[CH:3]=1.[CH2:14]([C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([F:23])[CH:17]=1)[CH3:15]>CCO.Cl>[CH2:11]([O:10][C:8](=[O:9])[C:7]1[C:2]([NH:22][C:19]2[CH:20]=[CH:21][C:16]([CH2:14][CH3:15])=[CH:17][C:18]=2[F:23])=[CH:3][C:4]([Cl:13])=[N:5][CH:6]=1)[CH3:12]

Participants

5

Reactant 2

HCID 600045Ethyl 4,6-dichloropyridine-3-carboxylateHCID 211613394-Ethyl-2-fluoroaniline

Product 1

HCID 58962865HCID 58962865, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

Ethyl 4,6-dichloronicotinate (31.62 g, 144.0 mmol) and 4-Ethyl-2-fluoro-phenylamine (20.0 g, 144.0 mmol) were dissolved in EtOH (200 mL), to which was added conc. HCl (6 drops) as for Example 1, alternate Step A to give 6-Chloro-4-(4-ethyl-2-fluoro-phenylamino)-nicotinic acid ethyl ester (46.50 g, 99%). (APCI+) calcd for C16H18ClFIN2O2 322.76 (M−1), found 321.0.

Sources & evidence

ORD record
ord-b0a07d902488479685d871a509cecae4
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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