Hydrochloric Acid → N-[2-Hydroxy-2-[3(2-quinolinylmethoxy)phenyl]ethyl]-2-pyridine carboxamide

HRID 2352347Notes

Reaction equation

HRID 2352347 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:19]2[O:23][C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[N:21][CH2:20]2)[CH:16]=[CH:17][CH:18]=1.Cl.[OH2:31]>C(#N)C>[OH:23][CH:19]([C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([O:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH:14]=1)[CH2:20][NH:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)=[O:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 139142654,5-Dihydro-5-[3-[(2-quinolinyl)methoxy]phenyl]-2-(2-pyridyl)-1,3-oxazole

Product 1

HCID 13914269N-[2-Hydroxy-2-[3(2-quinolinylmethoxy)phenyl]ethyl]-2-pyridine carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3.9 g (0.01 mol) of 4,5-dihydro-5-[3-[(2-quinolinyl)methoxy]phenyl]-2-(2-pyridyl)-1,3-oxazole in 100 ml of acetonitrile, 10 ml of water, and 1 ml of concentrated hydrochloric acid is heated on a steam bath for 5 hours. The solvents are evaporated and the residue is dissolved in a mixture of aqueous sodium bicarbonate and ethyl acetate. The ethyl acetate solution is separated and washed with dilute aqueous sodium chloride solution. The ethyl acetate solution is dried over anhydrous magnesium sulfate, filtered, and evaporated. The residue is dissolved in hot ethyl acetate and the solution is distilled with hexane to obtain crystals (2.2 g), m.p. 126°-129° C.

Workup

  1. customThe solvents are evaporated
  2. dissolutionthe residue is dissolved in a mixture of aqueous sodium bicarbonate and ethyl acetate
  3. customThe ethyl acetate solution is separated
  4. washwashed with dilute aqueous sodium chloride solution
  5. dry with materialThe ethyl acetate solution is dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionThe residue is dissolved in hot ethyl acetate
  9. distillationthe solution is distilled with hexane

Sources & evidence

ORD record
ord-637b22dc493643be814fa861d86c3580
Source dataset
uspto-grants-1989_10
Patent number
US04876346

Reaction notes

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