Sodium Hydroxide → HCID 68473089, compound

HRID 387680Notes

Reaction equation

HRID 387680 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:20]([O:22]C)=[O:21])[C:5]2[CH2:6][CH2:7][N:8]([CH:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[C:9](=[O:12])[C:10]=2[CH:11]=1.[OH-].[Na+]>O1CCOCC1>[CH3:1][C:2]1[CH:3]=[C:4]([C:20]([OH:22])=[O:21])[C:5]2[CH2:6][CH2:7][N:8]([CH:13]([CH2:14][CH2:15][CH3:16])[CH2:17][CH2:18][CH3:19])[C:9](=[O:12])[C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68469403HCID 68469403, compound

Product 1

HCID 68473089HCID 68473089, compoundYield 106.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

33 mg of methyl 7-methyl-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate are dissolved in 1 cm3 of dioxane at a temperature close to 20° C. 0.3 cm3 of a 1N aqueous solution of sodium hydroxide is added, then the reaction mixture is heated at a temperature close to 60° C. for 1 h. The mixture is then concentrated to dryness under reduced pressure (5 kPa), taken up by 10 cm3 of water and 15 cm3 of ethyl ether. The aqueous phase is decanted, washed with 10 cm3 of ethyl ether, acidified with 0.3 cm3 of a 2N aqueous solution of hydrochloric acid and taken up with 10 cm3 of dichloromethane. The organic phase is extracted, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure (5 kPa). 33.5 mg of 7-methyl-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid are obtained in the form of a colorless lacquer.

Workup

  1. customclose to 20° C
  2. temperaturethe reaction mixture is heated at a temperature
  3. customclose to 60° C. for 1 h
  4. concentrationThe mixture is then concentrated to dryness under reduced pressure (5 kPa)
  5. customThe aqueous phase is decanted
  6. washwashed with 10 cm3 of ethyl ether
  7. extractionThe organic phase is extracted
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-3ec256772cae46ceba3d17df1123b3da
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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