1-Propanol → HCID 22247318, compound

HRID 1107976Notes

Reaction equation

HRID 1107976 reaction equation
[CH2:1]([N:9]1[C:18]2[C:13](=[C:14]([CH3:24])[C:15]([CH2:20][C:21](=[O:23])N)=[C:16]([CH3:19])[CH:17]=2)[CH2:12][CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-].[Na+].[CH2:27]([OH:30])[CH2:28]C>O>[CH2:1]([N:9]1[C:18]2[C:13](=[C:14]([CH3:24])[C:15]([CH2:20][C:21]([O:30][CH2:27][CH3:28])=[O:23])=[C:16]([CH3:19])[CH:17]=2)[CH2:12][CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 10311-PropanolHCID 14798Sodium HydroxideHCID 22247339HCID 22247339, compound

Product 1

HCID 22247318HCID 22247318, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

1-Octyl-6-carbamoylmethyl-5,7-dimethyl-1,2,3,4-tetrahydroquinoline (2.5 g) was dissolved in n-propanol (50 ml) and a solution of NaOH (3.0 g) in water (30 ml) was added, which was followed by stirring at 130° C. for 20 hr under nitrogen. The organic layer of the reaction mixture was separated and the solvent was evaporated under reduced pressure. The residue was dissolved in water (300 ml) and washed with ethyl acetate (100 ml). The aqueous layer was adjusted to pH 1-2 with 6N hydrochloric acid and extracted with chloroform (200 ml). The chloroform layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained 1-octyl-6-carboxymethyl-5,7-dimethyl-1,2,3,4-tetrahydroquinoline was dissolved in ethanol (50 ml), and conc. hydrochloric acid (4 ml) was added, which was followed by stirring at 70° C. for 1 hr. The solvent was evaporated under reduced pressure. The residue was neutralized with saturated aqueous solution of sodium hydrogencarbonate and extracted with chloroform (100 ml). After washing with water, the chloroform layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: benzene) to give 1.0 g of oily 1-octyl-6-ethoxycarbonylmethyl-5,7-dimethyl-1,2,3,4-tetrahydroquinoline.

Workup

  1. customThe organic layer of the reaction mixture was separated
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in water (300 ml)
  4. washwashed with ethyl acetate (100 ml)
  5. extractionextracted with chloroform (200 ml)
  6. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. dissolutionThe obtained 1-octyl-6-carboxymethyl-5,7-dimethyl-1,2,3,4-tetrahydroquinoline was dissolved in ethanol (50 ml)
  9. additionconc. hydrochloric acid (4 ml) was added
  10. stirringby stirring at 70° C. for 1 hr
  11. customThe solvent was evaporated under reduced pressure
  12. extractionextracted with chloroform (100 ml)
  13. washAfter washing with water
  14. dry with materialthe chloroform layer was dried over anhydrous sodium sulfate
  15. customThe solvent was evaporated under reduced pressure
  16. customThe residue was purified by silica gel column chromatography (eluent: benzene)

Sources & evidence

ORD record
ord-96d39967be044f568a27cb5ee46921ed
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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