Water → HCID 15839869, compound

HRID 1377483Notes

Reaction equation

HRID 1377483 reaction equation
[CH3:1][N:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([CH2:18][CH2:19][C:20]([O:22]C)=[O:21])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:24].[OH-].[Na+].O>CO>[CH3:1][N:2]1[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:10]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 15839871HCID 15839871, compound

Product 1

HCID 15839869HCID 15839869, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.2 g (3.7 mmol) of methyl 2-methyl-1-oxo-3-phenyl-1,2-dihydroisoquinoline-4-propanoate are dissolved in 80 ml of methanol in a 250 ml round-bottomed flask, 0.25 g (6.25 mmol) of sodium hydroxide pellets and 1 ml of water are added and then the mixture is stirred at room temperature for 1 h and at reflux for 2 h. The mixture is cooled, the solvent is evaporated under reduced pressure, the residue is taken up in 50 ml of water and 50 ml of diethyl ether, and 36% hydrochloric acid is added dropwise. The insoluble material is collected by filtering, is washed with water and is dried. 0.91 g (2.96 mmol) of white solid is obtained. Melting point: 138°-140° C.

Workup

  1. temperatureat reflux for 2 h
  2. temperatureThe mixture is cooled
  3. customthe solvent is evaporated under reduced pressure
  4. addition50 ml of diethyl ether, and 36% hydrochloric acid is added dropwise
  5. customThe insoluble material is collected
  6. filtrationby filtering
  7. washis washed with water
  8. customis dried

Sources & evidence

ORD record
ord-18f3dd55c08a4fd79edddc0b9a0bf819
Source dataset
uspto-grants-1997_09
Patent number
US05665733

Reaction notes

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