Dichloromethane → HCID 15839871, compound

HRID 1377482Notes

Reaction equation

HRID 1377482 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](/[CH:18]=[CH:19]/[C:20]([O:22][CH3:23])=[O:21])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:24].C1CCCCC1.ClCCl>C(O)(=O)C.[Pd]>[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]([O:22][CH3:23])=[O:21])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:24]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 8078CyclohexaneHCID 15839878HCID 15839878, compound

Product 1

HCID 15839871HCID 15839871, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

0.25 g of 5% palladium-on-charcoal is added to a solution of 3.8 g (11.9 mmol) of methyl (E)-3-(2-methyl-1-oxo-3-phenyl-1,2-dihydroisoquinol-4-yl)prop-2-enoate in 100 ml of acetic acid and the suspension is subjected to hydrogenation in a Parr apparatus under pressure of approximately 0.3 MPa for 1 h at room temperature and then for 3 h at approximately 50° C. The catalyst is removed by filtering, the filtrate is concentrated under reduced pressure, ice-cold water, 200 ml of dichloromethane and 100 ml of 1N sodium hydroxide are added to the residue, the organic phase is separated, washed with water and dried over sodium sulphate and the solvent is evaporated under reduced pressure. The crude product is purified by chromatography on a column of silica gel, elution being carried out with a mixture of dichloromethane and ethyl acetate ranging from 100/0 to 70/30. After recrystallizing from a mixture of cyclohexane and dichloromethane, 2.69 g (8.37 mmol) of white solid are obtained. Melting point: 134°-135° C.

Workup

  1. waitfor 3 h at approximately 50° C
  2. customThe catalyst is removed
  3. filtrationby filtering
  4. concentrationthe filtrate is concentrated under reduced pressure, ice-cold water, 200 ml of dichloromethane and 100 ml of 1N sodium hydroxide
  5. additionare added to the residue
  6. customthe organic phase is separated
  7. washwashed with water
  8. dry with materialdried over sodium sulphate
  9. customthe solvent is evaporated under reduced pressure
  10. customThe crude product is purified by chromatography on a column of silica gel, elution
  11. additionbeing carried out with a mixture of dichloromethane and ethyl acetate ranging from 100/0 to 70/30
  12. customare obtained

Sources & evidence

ORD record
ord-9020cff99dc147c3a4782f92f76f4c96
Source dataset
uspto-grants-1997_09
Patent number
US05665733

Reaction notes

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