Hydrochloric Acid → HCID 18510854, compound

HRID 1370552Notes

Reaction equation

HRID 1370552 reaction equation
[CH:1]1([N:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>C(O)C.[Pd]>[CH:1]1([N:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18510807HCID 18510807, compound

Product 1

HCID 18510854HCID 18510854, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The compound (200 mg) obtained in step (c) just above was dissolved in a mixed solution (10.7 ml) of ethanol: concentrated hydrochloric acid=15:1. 10% Pd-C (60 mg) was added to the solution, followed by hydrogenation for 3.5 hr. Pd-C was removed by filtration through Celite. The filtrate was concentrated under the reduced pressure. Water was then added the residue. The mixture was extracted with ethyl acetate. The organic layer was then dried over anhydrous magnesium sulfate. The solvent was then removed by distillation to give 2-cyclohexyl-3,4-dihydro-2H-isoquinolin-1-one (168 mg).

Workup

  1. customPd-C was removed by filtration through Celite
  2. concentrationThe filtrate was concentrated under the reduced pressure
  3. additionWater was then added the residue
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
  6. customThe solvent was then removed by distillation

Sources & evidence

ORD record
ord-0b1aa93f61d14d2bbbdb7c9b6247c2b2
Source dataset
uspto-grants-2003_06
Patent number
US06583144B2

Reaction notes

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