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

HRID 2119048노트

반응식

HRID 2119048 반응식
[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

참가 물질

7

반응물 2

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

생성물 1

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

시약·촉매·용매 4

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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 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.

후처리

  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 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.

출처 및 근거

ORD 기록
ord-17b90e9fdb1f4a58a7aa257a1b60427b
출처 데이터셋
uspto-grants-1987_07
특허 번호
US04681940

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