Dimethylformamide → HCID 58294393, compound

HRID 521012Notes

Reaction equation

HRID 521012 reaction equation
S(Cl)([Cl:3])=O.CN(C)C=O.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([C:18]2[C:19]([C:24]([OH:26])=O)=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:15]=[CH:16][CH:17]=1>ClCCl>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([C:18]2[C:19]([C:24]([Cl:3])=[O:26])=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 52983911HCID 52983911, compound

Product 1

HCID 58294393HCID 58294393, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Thionyl chloride (8 mL) and N,N-dimethylformamide (few drops) are added to a solution of 3-(3-methoxy-phenyl)-pyridine-2-carboxylic acid (11.86 g) in dichloromethane (80 mL). The mixture is heated to 40° C. and stirred at this temperature overnight. The solution is then concentrated and the residue is taken up in toluene and concentrated again to give the crude title compound that is used without further purification in the next step. Yield: 12.80 g (crude).

Workup

  1. concentrationThe solution is then concentrated
  2. concentrationconcentrated again

Sources & evidence

ORD record
ord-a8326488ae1b49f2a4fbc810626535a1
Source dataset
uspto-grants-2016_05
Patent number
US09328072B2

Reaction notes

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