Sodium Carbonate → HCID 15239360, compound

HRID 1609493Notes

Reaction equation

HRID 1609493 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH:20](C(O)=O)[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:24])[N:12]2[CH3:25])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+]>CS(C)=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:24])[N:12]2[CH3:25])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 20081991HCID 20081991, compound

Product 1

HCID 15239360HCID 15239360, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 50 ml of a solution containing 9.00 g of 3-(4-t-butylphenyl)-4-hydroxycarbonyl-2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinoline in dimethylsulfoxide, 4.20 g of sodium carbonate was added and the mixture was allowed to react at 150° C. for 1 hour. After the reaction, the solvent was evaporated under reduced pressure, and 800 ml of water was added thereto, followed by extraction with ethyl acetate (100 ml×5). The combined organic layers were washed with water (300 ml×6) and then with brine, and were dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography [hexane/ethyl acetate (2/1)] to obtain 5.92 g of 3-(4-t-butylphenyl)-2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. additionwas added
  2. customto react at 150° C. for 1 hour
  3. customAfter the reaction
  4. customthe solvent was evaporated under reduced pressure, and 800 ml of water
  5. additionwas added
  6. extractionfollowed by extraction with ethyl acetate (100 ml×5)
  7. washThe combined organic layers were washed with water (300 ml×6)
  8. dry with materialwith brine, and were dried over anhydrous magnesium sulfate
  9. customAfter evaporating the solvent under reduced pressure
  10. customthe residue was purified by silica gel column chromatography [hexane/ethyl acetate (2/1)]

Sources & evidence

ORD record
ord-af8e177acf2743bea44b0552ea6bfb83
Source dataset
uspto-grants-1995_03
Patent number
US05401752

Reaction notes

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