Sodium Carbonate → HCID 19013340, compound

HRID 1729034Notes

Reaction equation

HRID 1729034 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][C:16]([CH:24]([CH3:26])[CH3:25])=[CH:17][CH:18]=3)[C:13](=[O:27])[N:12]2[CH3:28])=[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][C:16]([CH:24]([CH3:25])[CH3:26])=[CH:17][CH:18]=3)[C:13](=[O:27])[N:12]2[CH3:28])=[CH:9][CH:10]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 19013342HCID 19013342, compound

Product 1

HCID 19013340HCID 19013340, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

To 20 ml of a solution containing 2.70 g of 3-(4-tert-butylphenyl)-7-isopropyl-2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinoline- 4-carboxylic acid (mixture of diastereomers) in dimethylsulfoxide, 1.10 g of sodium carbonate was added and the resulting mixture was heated at 150° C. for 12 hours. After the reaction, the solvent was evaporated under reduced pressure and 200 ml of water was added thereto. The resultant was extracted with ethyl acetate (50 ml×3) The organiclayers were combined and washed with saturated aqueous sodium chloride solution and the resultant was dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by column chromatography on silica gel (hexane/ethyl acetate=5/1 v/v) to obtain 2.10 g of 3-(4-tertbutylphenyl)-7-isopropyl-2-methyl-l,2,3,4-tetrahydroisoquinoline-1-one.

Workup

  1. additionwas added
  2. customAfter the reaction
  3. customthe solvent was evaporated under reduced pressure and 200 ml of water
  4. additionwas added
  5. extractionThe resultant was extracted with ethyl acetate (50 ml×3) The
  6. washwashed with saturated aqueous sodium chloride solution
  7. dry with materialthe resultant was dried over anhydrous magnesium sulfate
  8. customAfter evaporating the solvent under reduced pressure
  9. customthe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=5/1 v/v)

Sources & evidence

ORD record
ord-6690e4e233b04273a1556d42de26523c
Source dataset
uspto-grants-1994_07
Patent number
US05330991

Reaction notes

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