Dimethylformamide → HCID 17817669, compound

HRID 350638Notes

Reaction equation

HRID 350638 reaction equation
[OH:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.CN(C)C=O.[O:28]([C:35]1[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O>[OH:1][C:2]1[C:3]([C:8]([NH:39][C:38]2[CH:37]=[CH:36][C:35]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:41][CH:40]=2)=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide3×HCID 8764(4-Aminophenoxy)benzeneHCID 134013-Hydroxypicolinic AcidHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 17817669HCID 17817669, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Hydroxypicolinic acid (1.39 g, 10.0 mmol) and 1.95 g (12.0 mmol) of carbonyldiimidazole were mixed into anhydrous N,N-dimethylformamide (hereinafter referred to as “DMF”) to prepare a suspension (30 ml). An anhydrous DMF solution (25 ml) of 1.85 g (10.0 mmol) of 4-phenoxyaniline was added dropwise to this suspension, and the reaction was allowed to proceed at room temperature overnight. Water (50 ml) was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the dried organic layer was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate-n-hexane) to give 1.24 g (yield 41%) of the title compound.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationthe dried organic layer was concentrated under the reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-e6cc57c5b2294106aec9efeadfdf8b2f
Source dataset
uspto-grants-2007_02
Patent number
US07183278B1

Reaction notes

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