Sodium Hydroxide → HCID 68473089, compound

HRID 387683Notes

Reaction equation

HRID 387683 reaction equation
Cl[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+].O1CCOC[CH2:27]1>>[CH3:27][C:2]1[CH:3]=[C:4]([C:20]([OH:22])=[O:21])[C:5]2[CH2:6][CH2:7][N:8]([CH:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[C:9](=[O:12])[C:10]=2[CH:11]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 68474742HCID 68474742, compound

Product 1

HCID 68473089HCID 68473089, compound

Procedure

33 mg of methyl 7-chloro-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate are dissolved in 6 cm3 of dioxane at a temperature close to 20° C. 1.8 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 1 h. The mixture is then concentrated to dryness under reduced pressure (5 kPa), taken up by 10 cm3 of ethyl ether and 10 cm3 of water. The aqueous phase is decanted, acidified with 1 cm3 of a 2N aqueous solution of hydrochloric acid. The reaction medium is washed two times with 10 cm3 of dichloromethane. The organic liquors are combined, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure (5 kPa). 215 mg of 7-methyl-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid are obtained in the form of yellow crystals that are used directly in the following reaction.

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. washThe reaction medium is washed two times with 10 cm3 of dichloromethane
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-4199167d99c74ae0b3e716d550a5d15a
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

Loading…