Water → HCID 59396637, compound

HRID 2383056Notes

Reaction equation

HRID 2383056 reaction equation
C[O-].[Na+].Cl[CH2:5][C:6]12OC(=O)C(=O)[N:7]1[CH2:8][CH2:9][C:10]1[C:15]2=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=1.C[CH2:24][O:25]C(C)=O.O>CO>[CH2:16]([C:13]1[CH:14]=[C:15]2[C:10]([CH2:9][CH2:8][N:7]=[C:6]2[CH2:5][O:25][CH3:24])=[CH:11][CH:12]=1)[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 67536351HCID 67536351, compound

Product 1

HCID 59396637HCID 59396637, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (9.46 g) was added to a suspension of 10b-(chloromethyl)-9-ethyl-6,10b-dihydro-5H-[1,3]oxazolo[2,3-a]isoquinoline-2,3-dione (14.0 mL) in MeOH (140 mL) under ice-cooling. The mixture was stirred at room temperature for 0.5 hours and then heated under reflux for 3 hours. EtOAc and water were added to the mixture, followed by filtration. The organic layer of the filtrate was collected, washed with saturated brine, and dried over magnesium sulfate. Activated carbon and silica gel were added thereto, followed by filtration. The filtrate was concentrated under reduced pressure to obtain 7-ethyl-1-(methoxymethyl)-3,4-dihydroisoquinoline (4.75 g).

Workup

  1. temperaturecooling
  2. temperatureheated
  3. temperatureunder reflux for 3 hours
  4. filtrationfollowed by filtration
  5. customThe organic layer of the filtrate was collected
  6. washwashed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. additionActivated carbon and silica gel were added
  9. filtrationfollowed by filtration
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-45cad4b0cc77491898deb83c4034804d
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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