Sodium Hydroxide → HCID 59526473, compound

HRID 1880606Notes

Reaction equation

HRID 1880606 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:20])=[C:5]2[C:10](=[C:11]([CH3:15])[C:12]=1[O:13][CH3:14])[CH:9](CC(N)=O)[NH:8][CH2:7][CH2:6]2.[OH-].[Na+]>O1CCOCC1>[CH3:1][O:2][C:3]1[C:4]([CH3:20])=[C:5]2[C:10](=[C:11]([CH3:15])[C:12]=1[O:13][CH3:14])[CH2:9][NH:8][CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68512777HCID 68512777, compound

Product 1

HCID 59526473HCID 59526473, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6,7-Dimethoxy-5,8-dimethyl-1,2,3,4-tetrahydroisoquinoline acetamide (396 mg) was dissolved in 1,4-dioxane (10 ml). NaOH (10 ml, 2M aq.) was added and the mixture was refluxed for 21 h. Organic solvents were evaporated and the aq. residue was extracted with dichloromethane (4×20 ml). Combined organics were dried (MgSO4), filtered and evaporated. The product was purified by flash chromatography using EtOAc/MeOH/Et3N (20/2/1→16/4/1) as eluent to give 116 mg (42%) of 6,7-dimethoxy-5,8-dimethyl-1,2,3,4-tetrahydroisoquinoline as a clear, oily residue.

Workup

  1. temperaturethe mixture was refluxed for 21 h
  2. customOrganic solvents were evaporated
  3. extractionthe aq. residue was extracted with dichloromethane (4×20 ml)
  4. dry with materialCombined organics were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-ca0953aa28464c81a9a5b1bfa71aa4f0
Source dataset
uspto-grants-2012_11
Patent number
US08318768B2

Reaction notes

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