Dimethylformamide → 6-Morpholinonicotinoyl Chloride

HRID 353828

Reaction equation

HRID 353828 reaction equation
CN(C)C=O.[C:6](Cl)(=O)[C:7]([Cl:9])=[O:8].[O:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:26]=[CH:25]C(C(O)=O)=[CH:20][N:19]=2)[CH2:14][CH2:13]1>C(Cl)(Cl)Cl>[O:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:26]=[CH:25][C:6]([C:7]([Cl:9])=[O:8])=[CH:20][N:19]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 27764606-Morpholinonicotinic Acid

Product 1

HCID 27764616-Morpholinonicotinoyl Chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N,N-Dimethylformamide (1 mL) was slowly added to a solution of oxalyl chloride (0.13 g, 1 mmol) in chloroform (5 mL). 6-Morpholinonicotinic acid (0.21 g, 1 mmol) was added and the reaction mixture was stirred for 15 minutes. The reaction mixture was concentrated under vacuum, diluted with toluene and then concentrated under vacuum to provide 6-morpholinonicotinoyl chloride. This material was kept under vacuum at ambient temperature overnight and then used in the next step.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additiondiluted with toluene
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ab0dabb6d4284df1a5c29527e5cd2f08
Source dataset
uspto-grants-2004_06
Patent number
US06756382B2

Linked notes

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