Methyl Picolinimidate → 3-[2-(Pyridin-2-yl)-4,5-dihydro-1,3-oxazol-5-yl]phenol

HRID 2352345Notes

Reaction equation

HRID 2352345 reaction equation
[CH:1]1[CH:6]=[C:5]([OH:7])[CH:4]=[C:3]([CH:8]([OH:11])[CH2:9][NH2:10])[CH:2]=1.Cl.CO[C:15]([C:17]1[N:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=N>O1CCCC1.C(OCC)(=O)C.O.C(#N)C>[OH:7][C:5]1[CH:4]=[C:3]([CH:8]2[O:11][C:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][N:22]=3)=[N:10][CH2:9]2)[CH:2]=[CH:1][CH:6]=1

Participants

7

Reactant 2

HCID 152260Methyl PicolinimidateHCID 3016408Benzenemethanol, alpha-(aminomethyl)-3-hydroxy-, hydrochloride (1:1)

Product 1

HCID 139142643-[2-(Pyridin-2-yl)-4,5-dihydro-1,3-oxazol-5-yl]phenol

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (±) norphenylephrine hydrochloride (10 g, 0.05 mol) and methyl iminopicolinate (8 g, 0.059 mol) in tetrahydrofuran (300 ml) is heated to reflux for 16 hours. The mixture is dissolved in ethyl acetate and water. The aqueous layer is extracted twice with ethyl acetate. The combined ethyl acetate solutions are washed twice with dilute aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated to dryness to obtain a partially crystalline material. This material is triturated with ethyl ether to obtain crystals. These crystals are dissolved in hot acetonitrile and the hot solution is filtered and allowed to cool. The crystals (4 g) are filtered off, washed with acetonitrile and dried in vacuo, m.p. 139°-141° C.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 16 hours
  3. extractionThe aqueous layer is extracted twice with ethyl acetate
  4. washThe combined ethyl acetate solutions are washed twice with dilute aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated to dryness
  7. customto obtain a partially crystalline material
  8. customThis material is triturated with ethyl ether
  9. customto obtain crystals
  10. filtrationthe hot solution is filtered
  11. temperatureto cool
  12. filtrationThe crystals (4 g) are filtered off
  13. washwashed with acetonitrile
  14. customdried in vacuo, m.p. 139°-141° C.

Sources & evidence

ORD record
ord-b28d446b160a49a6985e79154f678e63
Source dataset
uspto-grants-1989_10
Patent number
US04876346

Reaction notes

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