Hydrochloric Acid → HCID 21071543, compound

HRID 1666902Notes

Reaction equation

HRID 1666902 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:9]=[CH:10][CH:11]=1.Cl.O>C1COCC1>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[NH:12][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[CH:2]=[O:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 21071444HCID 21071444, compound

Product 1

HCID 21071543HCID 21071543, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve (3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yl-amine (10.32 g, 42.6 mmol) in THF (150 mL). Add concentrated HCl solution (37.5 mL) and stir the solution at room temperature overnight. Concentrate the reaction, treat with water, and extract with CH2Cl2. Wash the organic extract with water, dry (Na2SO4) and concentrate to give the crude product. Purification by flash chromatography (hexanes/EtOAc (7:3)) provides the title compound as a yellow solid.

Workup

  1. concentrationConcentrate
  2. customthe reaction
  3. extractionextract with CH2Cl2
  4. washWash the
  5. extractionorganic extract with water
  6. dry with materialdry (Na2SO4)
  7. concentrationconcentrate
  8. customto give the crude product
  9. customPurification by flash chromatography (hexanes/EtOAc (7:3))

Sources & evidence

ORD record
ord-55a5426a7ef74ed5b4610414fdd9f29d
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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