Sodium Hydroxide → HCID 68471625, compound

HRID 387676Notes

Reaction equation

HRID 387676 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]([C:27]([O:29]C)=[O:28])[C:12]2[CH2:13][CH2:14][N:15]([CH:20]([CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])[C:16](=[O:19])[C:17]=2[CH:18]=1)#[N:2].[OH-].[Na+]>O1CCOCC1>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]([C:27]([OH:29])=[O:28])[C:12]2[CH2:13][CH2:14][N:15]([CH:20]([CH2:21][CH2:22][CH3:23])[CH2:24][CH2:25][CH3:26])[C:16](=[O:19])[C:17]=2[CH:18]=1)#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68473665HCID 68473665, compound

Product 1

HCID 68471625HCID 68471625, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

178 mg of methyl 7-(2-cyanophenyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate are dissolved in 3.6 cm3 of dioxane at a temperature close to 20° C. 1.1 cm3 of a 1N aqueous solution of sodium hydroxide are added, then the reaction mixture is heated at a temperature close to 60° C. for 30 min. The mixture is then concentrated to dryness under reduced pressure (5 kPa), taken up by 20 cm3 of water and 20 cm3 of ethyl ether. The aqueous phase is washed with 5 cm3 of ethyl ether, acidified with 2 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). 171 mg of 7-(2-cyanophenyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid are obtained in the form of a white foam.

Workup

  1. customclose to 20° C
  2. temperaturethe reaction mixture is heated at a temperature
  3. customclose to 60° C. for 30 min
  4. concentrationThe mixture is then concentrated to dryness under reduced pressure (5 kPa)
  5. washThe aqueous phase is washed with 5 cm3 of ethyl ether
  6. extractionThe organic phase is extracted
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-7c4f0bea07244494aa62a67c588124d3
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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