HCID 14685729, compound → HCID 14685732, compound

HRID 1088794Notes

Reaction equation

HRID 1088794 reaction equation
O=C1[O:7][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:11]3[CH:12]([O:15][CH3:16])[CH2:13][CH2:14][N:3]1[C:4]=23>[OH-].[Na+].CO>[OH:7][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:4]=1[NH:3][CH2:14][CH2:13][CH:12]2[O:15][CH3:16]

Participants

4

Reactant 1

HCID 14685729HCID 14685729, compound

Product 1

HCID 14685732HCID 14685732, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

6,7-Dihydro-3-oxo-7-methoxy-1H,3H,5H-pyrido[3,2,1-ij][3,1]benzoxazine (4.3 g) was dissolved in a mixture of 10% aqueous solution of sodium hydroxide and methanol (1:10 v/v, 55 ml), and the mixture was refluxed for 2 hours. After distilling off the solvent, the resulting residue was extracted with dichloromethane. The extract was washed with water and dried, the solvent was removed. The resultant residue was purified by silica gel column chromatography [eluent: n-hexane-ethyl acetate (4:1 v/v)]to give 8-hydroxymethyl-4-methoxy-1,2,3,4-tetrahydroquinoline (2.4 g).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. distillationAfter distilling off the solvent
  3. extractionthe resulting residue was extracted with dichloromethane
  4. washThe extract was washed with water
  5. customdried
  6. customthe solvent was removed
  7. customThe resultant residue was purified by silica gel column chromatography [eluent

Sources & evidence

ORD record
ord-2fbda94158394714a01c447f25f34785
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

Loading…