Picolinic acid → Ethyl chloroformate

HRID 842307Notes

Reaction equation

HRID 842307 reaction equation
N1C=CC=C[C:2]=1[C:7]([OH:9])=[O:8].C(N(CC)CC)C.[C:17]([Cl:23])(=[O:22])C(C)(C)C>ClCCl>[Cl:23][C:7]([O-:9])=[O:8].[CH2:7]([O:8][C:17]([Cl:23])=[O:22])[CH3:2]

Participants

6

Reactant 3

HCID 1018Picolinic acidHCID 8471TriethylamineHCID 62493Pivaloyl chloride

Product 2

HCID 10928Ethyl chloroformateHCID 21226386Carbonochloridate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Picolinic acid compound 4 is reacted with an organic base, e.g., triethylamine, followed by an acid chloride, e.g., pivaloyl chloride or a chloroformate, e.g., C2H5OCOCl in a suitable solvent such as dichloromethane at a temperature of about −30° C. to 0° C. to give a mixed anhydride. To the mixture is added NH2R5 at a temperature of −30° C. to 0° C. either neat or as a solution in a suitable solvent to form amide compound 2.

Sources & evidence

ORD record
ord-7f177fef3337496494122e40d32ee6f7
Source dataset
uspto-grants-2002_04
Patent number
US06372909B1

Reaction notes

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