Water → 3-(4,4-Dimethyl-4,5-dihydro-1,3-oxazol-2-yl)pyridine

HRID 1650704Notes

Reaction equation

HRID 1650704 reaction equation
[C:1]([O:9][CH3:10])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[NH2:11][C:12](C)([CH3:15])[CH2:13]O.O>C1(C)C=CC=CC=1>[CH3:13][C:12]1([CH3:15])[CH2:10][O:9][C:1]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)=[N:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 7151Methyl NicotinateHCID 118072-Amino-2-methyl-1-propanol

Product 1

HCID 27361293-(4,4-Dimethyl-4,5-dihydro-1,3-oxazol-2-yl)pyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 69 g (0.500 mol) of methyl nicotinoate and 45 g (0.500 mol) of 2-amino-2,2,dimethyl-ethanol in 600 ml of toluene was refluxed with a water separator overnight. The solvent was removed in vacuo, 300 ml of water added, and the aqueous solution extracted with 3×300 ml of dichloromethane. Drying of the organic phase over magnesium sulphate and evaporation in vacuo gave a red oil which was filtered through silica gel (eluent: methanol/ether=1/19). Removal of solvents in vacuo gave a yellow oil, 86. Yield: 30.0 g (0.170 mol, 34%).

Workup

  1. customThe solvent was removed in vacuo, 300 ml of water
  2. additionadded
  3. extractionthe aqueous solution extracted with 3×300 ml of dichloromethane
  4. dry with materialDrying of the organic phase over magnesium sulphate and evaporation in vacuo
  5. customgave a red oil which
  6. filtrationwas filtered through silica gel (eluent: methanol/ether=1/19)
  7. customRemoval of solvents in vacuo
  8. customgave a yellow oil, 86

Sources & evidence

ORD record
ord-f5557c81f3e44ff39572cf4f8a0a6e71
Source dataset
uspto-grants-1990_05
Patent number
US04925858

Reaction notes

Loading…