Methanol → Methyl 4-chloronicotinate

HRID 870912Notes

Reaction equation

HRID 870912 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=1.[C:11](Cl)(=O)C(Cl)=O.CN(C=O)C.CO>C(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 8182294-Chloronicotinic acid

Product 1

HCID 12574055Methyl 4-chloronicotinateYield 123%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloronicotinic acid (0.5 g, 3.17 mmol) in CH2Cl2 (60 mL) was added oxalyl chloride (1.007 g, 7.93 mmol) dropwise at room temperature followed by the addition of DMF (0.4 mL). The solution was stirred at room temperature for 3 h. Methanol (1.9 mL, 46.8 mmol) was added dropwise and the clear solution was further stirred for 30 min. The solvent was evaporated under reduced pressure to yield methyl 4-chloronicotinate (0.67 g, 3.90 mmol, 50% yield). LCMS (ESI) m/e 172.5 [(M+H)+, calcd for C7H7ClNO2 172.0]; LCMS retention time (Method D): tR=1.15 min.

Workup

  1. stirringthe clear solution was further stirred for 30 min
  2. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-22a825960fc4455f92e750656f62d5fa
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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