Trifluoroacetic acid → HCID 54241356, compound

HRID 361343Notes

Reaction equation

HRID 361343 reaction equation
[N:1]1([C:7]([O:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:15]=2[N:16]=CN(C)C)=[O:8])CCCCC1.F[C:22](F)(F)[C:23](O)=O>O>[N:12]1([NH:1][C:7]([O:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:15]=2[NH2:16])=[O:8])[CH2:23][CH2:22][CH2:15][CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67749072HCID 67749072, compound

Product 1

HCID 54241356HCID 54241356, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture prepared from 4-[[(dimethylamino)methylene]amino]-3-pyridinol 1-piperdine carboxylate (3.4 g), trifluoroacetic acid (11 mL) and water (6 mL) was refluxed for a half hour. The reaction mixture was concentrated, dissolved in saturated NaHCO3 (50 mL) and extracted three times with ethyl acetate (450 mL). The extract was dried (MgSO4), concentrated, and triturated with diethyl ether/pentane (1:2) to yield 2.27 g of solid. This was recrystallized from ethyl acetate and dried under high vacuum and refluxing acetone for 4 hours to yield 1.58 g of crystals, m.p. 134° C. (dec.).

Workup

  1. temperaturewas refluxed for a half hour
  2. concentrationThe reaction mixture was concentrated
  3. dissolutiondissolved in saturated NaHCO3 (50 mL)
  4. extractionextracted three times with ethyl acetate (450 mL)
  5. dry with materialThe extract was dried (MgSO4)
  6. concentrationconcentrated
  7. customtriturated with diethyl ether/pentane (1:2)

Sources & evidence

ORD record
ord-eaccb072a2834775a5145cb2b2b4a079
Source dataset
uspto-grants-1999_02
Patent number
US05866565

Reaction notes

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